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Synthesis of rutaecarpine analogues by borrowing hydrogen strategy Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 Liangfeng Wang, Linfeng Zhang, Chao Zhou, Tiantian Gou, Nanying Chen, Ke Feng, Shiqing Li, Jun-Cheng Su, Jingxian Yu, Guixia Wang, Xiangfei Kong
A series of rutaecarpine analogues were synthesized in 11–90% yields via an iron (II) phthalocyanine-catalyzed N-alkylation reaction of 3-hydroxyethyl quinazolinone-linked indole. Mechanistic investigation revealed that the formation of C-N bonds in the cyclization reaction occurs through intramolecular borrowing hydrogen annulation. The crucial intermediates in this process were verified by LC-MS
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Visible Light Photoredox-Catalyzed Three-Component Reaction of Styrenes with Malonic Esters and CO2 Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 Alisa D. Kharlamova, Alexei D. Averin, Grigoriy N. Bondarenko, Anton Abel, Irina Beletskaya
A visible light photoredox-catalyzed bifunctionalization of styrenes with malonic esters and CO2 to form two C(sp3)–C bonds has been developed. The reaction proceeds at room temperature with 0.1 mol% of the organic photocatalyst (4DPAIPN) and cesium carbonate as a base at a CO2 pressure of 4 atm. This results in the production of 3-arylpropane-1,1,3-tricarboxylic acid esters in yields ranging from
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Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents with Alkenyl Carbonate Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 Hongjian Qin, Xingbang Yang, Emmanuel Mintah Bonku, Fuqiang Zhu, Safomuddin Abduahdi, Peng Yang, Jingshan Shen, Haji Akber Aisa
Herein, we report the alkylation of alkenyl carbonates using alkyl Grignard reagents and iron catalysis to generate C(sp2)–C(sp3) bonds and provide synthetically useful yields over a range of substrates. The transformation allows the alkylation of a wide range of substrates, including aromatic rings, alkanes, cycloalkanes, heterocycles. This reaction has introduced a new family of electrophiles to
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Thiocarbonyl-Directed Iridium-Catalyzed C–H Silylation of Indoles and Pyrroles with Hydrosilanes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 Yi Cheng, Jingyi Zhan, Lei Wang, Houyun Teng, Li-Wen Xu, Lei Yang
Herein, hydrogen-acceptor-free C2-selective iridium-catalyzed C–H silylation of indoles and pyrroles with hydrosilanes via C(sp2)–H bond activation to generate the desired silylated products is presented. The developed protocol allows for the C–H silylation of a wide range of functionalized indoles with monohydrosilanes under iridium catalysis. Significantly, this process represents a rare silylation
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Visible-Light-Induced Stereoselective C(sp3)−C(sp3)−H Glycosylation for the Synthesis of C-Glycoamino Acid Derivatives Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 Guanghui Lv, Pingping Ruan, Hui Sun, Yafei Zhu, Mi Wang, Cuimei Zhang, Jian Chen, Li Guo, Yong Wu
Chiral C-Glycosyl amino acids are prevalent structural motifs found in pharmaceuticals and natural products, making them a significant dimension for exploration in modern pharmaceutical and medicinal chemistry. However, the current synthesis methods for these compounds face numerous environmental and practical challenges, highlighting the critical need to establish more sustainable approaches. Herein
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Photocatalytic Oxidation of α-Substituted Amines to Lactams/Amides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-24 UTPAL DAS, Manish Kumar, Pawan Kumar
We, herein, report a base free, photocatalytic decyanation of α-aminonitriles. A range of amides and lactams were obtained in 52-95% yields. Control experiments indicate O2 as an amide/lactam oxygen source and the reaction (lactam formation) follows radical pathway via dioxetanimine species. This methodology also applied for α-ester/aldehyde substituted pyrrolidines in the presence of a base, probably
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Recyclable All-in-one Organo-Photo-Auxiliaries Enabling (sp3)C–(sp3)C Coupling Reactions with Diverse Functionalities Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-23 Samjhana Maharjan, Ravi Dakoju Kishore, Bella Albano, Pamela A. Ondiek, Joseph M. O’Shea, Angel G. Cosme-Hernandez, Donald J Wink, Steven Lopez, Barry C. Pemberton, Anoklase Jean-Luc Ayitou
Photochemical C–C coupling reactions can be tailored to environmentally benign industrial chemical processes and preparations of valuable pharmaceuticals. Yet, recent approaches in this area are limited to using precious transition metal coordination complexes that facilitate light absorption and redox processes with benchtop chemicals. Herein, we propose a new paradigm that involves all-in-one or
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Copper-Catalyzed Tandem Cyclization of 2-(Alkynylaryl)acetonitriles and Amines: Access to 3-Hydroxyisoindolinones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-23 Wanqing Wu, Jiatian Li, Lin Pan, Xiangwen Tan, Huanfeng Jiang
Herein, we describe an approach to the synthesis of 3-hydroxyisoindolinone derivatives via copper-catalyzed tandem cyclization of 2-(alkynylaryl)acetonitriles and amines. This reaction is compatible with 2-(alkynylaryl)acetonitriles and primary alkyl amines containing various functional groups, providing the corresponding 3-hydroxyindolinone derivatives with yields ranging from 44% to 82% (medium to
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Visible-light-mediated vinyl-thiophosphate formation via three-component denitrative cross-coupling reaction Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-23 Xiao-Ying Huang, Yu Zhu, Zong-Cang Ding, Hai-Tao Tang, Ying-ming Pan, Wengui Duan, Fei-Hu Cui
A three-component denitrative cross-coupling reaction mediated by visible light has been developed. Various 2-arylvinyl thiophosphate compounds were synthesized with moderate-to-good yields using cheap, nontoxic, nonvolatile, and nonhygroscopic elemental sulfur (S8) as the raw material. These transformations allow the direct formation of C-S and S-P bonds without metal catalyst via a one-pot procedure
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Ag‐Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition of N‐2,2,2‐Trifluoroethylisatin Ketimines with Conjugated Exocyclic Double Bond: Access to Pyrrolidines with Four Consecutive Stereocenters Including Two Adjacent Spiro‐Quaternary Centers Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-23 Ji-Hong Liu, Yan-Ping Zhang, Zhen-Hua Wang, Ji-Hong Lu, Lei Yang, yong you, Jian-Qiang Zhao, Ming-Qiang Zhou, Weicheng Yuan
Ag‐catalyzed enantioselective 1,3‐dipolar cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines with conjugated exocyclic double bond including α‐alkylidene succinimides and aurone derivatives was developed for the first time. Using a catalyst system consisting of a ferrocenyl P,N‐ligand and AgNO2, the reaction provides a facile method for the construction of chiral pyrrolidines bearing four consecutive
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Solvent‐ and Temperature‐Switched Chemoselectivity: Controlled Synthesis of Diverse Pyrazolo[5,1‐a]isoquinolines Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-23 Chunmei Li, Meng Xu, Chen Wang, Furen Zhang, Zhenlu Shen
. Divergent synthesis of two types of functionalized pyrazolo[5,1‐a]isoquinolines was established via a one‐pot two‐step protocol involving a tunable dehydrogenation process and deacylative oxidation accompanied by elimination of the HNO2 pathway. Key attributes of the procedure included the initial formation of C,N‐cyclic‐N’‐acyl azomethine imines and subsequent switchable chemoseletivity that either
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Flavin–Iodine‐Catalyzed Aerobic Oxidative Tandem C(sp3)–H Imination and Amination: Synthesis of Fluorescent Imidazo[1,5‐a]pyridines from Pyridylmethanes and Aminomethanes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-21 Tatsuki Fukuda, Hazuki Miyake, Sota Abe, Fumitoshi Yagishita, Hiroki Iida
Aerobic oxidative tandem C(sp3)–H imination and amination between pyridylmethane and aminomethane derivatives was demonstrated using a flavin–iodine‐coupled catalyst. This method provides a simple and atom‐economical synthesis of various 1,3‐substituted imidazo[1,5‐a]pyridines with fluorescent properties. The flavin–iodine catalyst efficiently promoted multiple reactions, including the oxygenation
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Tandem Synthesis of 3,5-Dihydrocyclopenta[de]quinolin-2(1H)-one Scaffolds from α-Bromocarbonyls and α-Diazoesters under Copper and Palladium Catalysis Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-18 Shuwei Li, Linqi Wang, Shangyuan Wang, Jun Ying
A Cu/Pd-catalyzed tandem radical cyclization and C-H activation/carbene insertion of α-bromocarbonyls with α-diazoesters has been developed for the construction of fused quinolin-2(1H)-one scaffolds. The reaction proceeded well to afford a series of 3,5-dihydrocyclopenta[de]quinolin-2(1H)-one derivatives. Additionally, bioactive molecules such as sesamol and estrone could be modified by using this
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Synthesis of Aza-S(VI) Fluorides and Primary Sulfonimidamides from Sulfinylamines Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-18 Michael Andresini, Laura Marraffa, Defne Şerbetçi, Philipp Natho, Marco Colella, Leonardo Degennaro, Renzo Luisi
Aza-S(VI) fluorides are crucial compounds in the synthesis of various S(VI) derivatives, which find broad applications in drug discovery. However, the synthesis of sulfonimidoyl and sulfondiimidoyl fluorides have been relatively underexplored, often requiring lengthy reaction sequences and/or the use of hazardous gaseous reagents. In this study, we present a rapid one-pot method for producing sulfonimidoyl
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Exploring Ferrocenyl Imine-Phosphane Complexes in Gold(I) Redox Switchable Catalysis and the Role of the “Magic Blue” Oxidant. Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-18 J. C. Pérez-Sánchez, R. P. Herrera, M. C. Gimeno
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Copper-Catalyzed Cross Coupling Reaction of Alkyl Bromides with (DMPU)2Zn(Rf)2 Reagent: A Method for the Synthesis of Perfluoroalkylated Compounds Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-17 Bosheng Liu, Xujuan Jiang, Yanshan Song, Shiwen Liu, Xiaodong Xiong, Xiaojun Zeng
A method for the copper-catalyzed cross-coupling of alkyl bromides with a range of (DMPU)2Zn(Rf)2 reagents has been developed. This protocol tolerates multiple functional groups and provides broad access to aliphatic perfluoroalkylated compounds. The applicability of this procedure is demonstrated in the late-stage functionalization of drug analogues.
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TMSOTf Mediated Aminocyclization/[1,3]-Sulfonyl Migration on N-Homopropargyl Hydroxylamines for the Stereoselective Synthesis of 3-Sulfonyl Cyclic Nitrones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-17 Santosh Gharpure, Showkat A. Hajam, Dharmendra Vishwakarma
TMSOTf-mediated 5-endo-dig aminocyclization followed by N- to C-[1,3]-sulfonyl migration on N¬-homopropargyl hydroxylamines gave diastereoselective access to trisubstituted 3-sulfonyl cyclic nitrone (3-sulfonyl pyrroline N-oxide) derivatives. The synthetic utility of the 3-sulfonyl cyclic nitrone products was demonstrated through the diastereoselective synthesis of the sulfonyl-substituted nonaromatic
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Stereoselective N-Heterocyclic-Carbene-Catalyzed Spiroannulation as an Access Towards Spirobenzofuranone-Fused Cyclohexenones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-17 Ladislav Lóška, Vojtěch Dočekal, Daniel Čermák, Simona Petrželová, Milan Pour, Ivana Cisařová, Klara Konečná, Ondřej Janďourek, Jan Vesely
In this work, we present an organocatalytic spiroannulation method that provides access to spirocyclic benzofuran-2-ones. The reaction proceeds via the generation of an azolium dienolate from an α-bromo-α,β-unsaturated aldehyde using a chiral N heterocyclic carbene, followed by annulation with benzofuran-2-one-derived alkenes. The resulting chiral spirobenzofuranone-fused cyclohexenones were obtained
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Visible-Light-Induced Deaminative Alkylation for the Synthesis of Chroman-4-one Derivatives via EDA Complexes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-17 Jinke Yan, Yuting Leng, Yangjie Wu
A visible-light-mediated synthesis of 3-alkyl- substituted chroman-4-one derivatives via deaminative alkylation of amino acid derived Katritzky salts and tandem cyclization with o-(allyloxy)arylaldehydes has been developed. This approach exhibits a certain functional-group compatibility with 31 examples and affords desired products in yields of 16% to 88%. Mechanistic research results suggests that
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Recent Advances in Visible-Light-Mediated Synthesis of Phosphorylated Heterocycles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-17 Teck-Peng Loh, Fanlin Zeng, Zhenhua Jia
Organophosphorus compounds, especially phosphorylated heterocycles, are gaining increasing attention in the fields of materials science, pharmaceuticals, and agrochemistry due to their excellent biological activities. Consequently, the exploration of green and efficient methods for the synthesis of phosphorylated heterocycles has garnered significant interest from organic chemists. In recent years
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Modular Access to Aryl Quinolinyl Ketones via Visible Light-Induced Palladium-Catalyzed Aldehyde C-H Bond Arylation of Quinoline-8-Carbaldehydes with Arylboronic Acid Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-16 Subhash Ghosh, Dinesh Thakur, Mahesh Sonawane, Raj Patel, Nileshkumar Rathod, Sachinkumar Patel, Dharmik Patel
This article describes the development of a room-temperature visible light-induced palladium-catalyzed directed aldehyde C-H bond arylation to access aryl quinolinyl ketones. In this pathway, the Pd catalyst plays a dual role by harvesting light as a photocatalyst and catalyzing the chemical transformation via C-H bond activation. This process is general to synthesize a range of aryl quinolinyl ketones
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Photocatalyzed Arylthiolation/Cyclization of 3-(2-(Ethynyl)phenyl)quinazolinones with Disulfides towards Arylthiolated Quinolino[2,1-b]quinazolinones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-16 Fanlin Zeng, Jinwei Yuan, Junru Jiang, Meiyue Zhang, Sanyu Zhang, Yanli Yin, Liangru Yang, Yongmei Xiao, Lingbo Qu
An approach to the synthesis of arylthiolated quinolino[2,1-b]quinazolinones has been developed using unactivated alkynes containing quinazolinones and diaryldisulfides under visible light irradiation. The procedure entails a sequential radical arylthiolation and cyclization reaction. A possible radical mechanism has been investigated and proven as a single electron transfer (SET) procedure.
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Controllable Synthesis of Oxa-/Thia-spirohydroquinolines by [3+(2+1)] Annulation of Aromatic Amines with Bimolecular O/S-Heterocyclic Ketones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-16 Lan Mei, Mu-Han Li, Wen-Chan Tian, Wei-Qian Fan, Liu-Bin Li, Qiang Li, Cai Zhai, Chen Zhu, Wen-Ting Wei
[3+(2+1)] Annulation represents the most straightforward and atom-economical strategies in organic synthesis for the efficient construction of diverse cyclic structural units and complex molecules. Herein, we present a Lewis acid Sc(OTf)3-catalyzed controlled synthesis of two different regioselective oxa/thio-spirohydroquinolines (C=C at the α/β-site of O/S-atom) from aromatic amines and bimolecular
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Divergent Synthesis of (CF3)-Indazolo[3,2-a]isoquinolines with Potent Photophysical Property and Anticancer Activity from 3-Aryl-1H-indazoles and Sulfoxonium Ylides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-15 Qianting Zhou, Shengnan Yan, Chunhua Ma, Yijun Gong, Xinying Zhang, Xuesen Fan
Transition-metal-catalyzed inert C−H bond functionalization using sulfoxonium ylides as metal carbene surrogates to replace the explosive and labile diazo compounds is synthetically attractive. Presented herein is a divergent synthesis of (CF3)-indazolo[3,2-a]isoquinoline derivatives based on C−H bond activation-initiated cascade reactions of 3-aryl-1H-indazoles with sulfoxonium ylides. The formation
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Advances in Exploring Mechanisms of Oxidative Phenolic Coupling Reactions Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-15 Haeun Choi, Sung-Eun Suh, Houng Kang
Biphenolic compounds serve as important scaffolds for the development of biologically active molecules. Among the methods for the synthesis of biarenols, oxidative coupling, which directly forms a C–C bond, has been extensively explored in various metal-catalyzed (V, Cr, Co, Fe, Cu, etc.) reactions, electrochemical reactions, and photochemical reactions over the decades. While the exact mechanisms
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One-pot Transformation Strategy of o-Hydroxyphenyl propargylamines for Modular Access to 3-Functionalized Benzofurans Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-15 Xinwei He, Mengdi Wu, Yanan Liu, Yangzilin Kong, Binbin Fei, Qiang Tang
A one-pot strategy to C3-functioanlized benzofurans is achieved from o-hydroxyphenyl propargylamines (o-HPPAs). 3-Aminobenzofurans were obtained in 64-96% yields through the cascade alkyne-allene tautomerization and 5-exo-dig annulation of o-HPPAs in the presence of KOH/NaOtBu as the fruitful base combination. Moreover, with bench-top benzenesulfinates and diphenylphosphine oxide as nucleophiles, a
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Emerging Trends for the Direct Synthesis of Dithiocarbamates Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-15 Jiawei He, Xuesi Zhou, Xiang Liu
Dithiocarbamates are common structural motifs in various bioactive compounds, attracting considerable attention due to their wide-ranging applications in organic synthesis, material science, agrochemicals, and the pharmaceutical industry. Given the significant bioactivity and extensive applications of dithiocarbamates, the continuous pursuit of their efficient and diverse synthetic methods remains
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Intermolecular Gold-Catalyzed Nitrene Transfer Employing Aryl Azides: An Access to 7-Functionalized 2‑Aminoindoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-12 George Puskov, Nikolay Shcherbakov, Vadim Kukushkin, Alexey Dubovtsev
We report on intermolecular gold-catalyzed nitrene transfer, utilizing o-functionalized aryl azides as nitrene transfer reagents. This catalytic reaction provides a modular route to 7-functionalized 2-aminoindoles. Due to the optimized reaction conditions (toluene, 80–100 °С), a variety of functional substituents proved compatible (36 examples; yields up to 98%). The reaction can be performed using
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Photoinduced Radical Borylation of Robust Carbon−Heteroatom Bonds Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-11 Ya-Ming Tian, Xiang Pu, Alejandro Heredero Sánchez, Wagner Silva, Ruth M. Gschwind, Burkhard Koenig
Photoinduced borylation has emerged as a valuable strategy for synthesizing arylboronic esters. However, photochemical transformations involving inert bonds such as C(sp2)−F bonds are still challenging. Herein, we report a straightforward and operationally simple method for the activation of various inert carbon−heteroatom bonds, enabling the synthesis of diverse arylboronic esters without the need
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Visible-Light-Induced C−H Silylation of Azauracils with Hydrosilanes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-11 Yongqi Yu, Mengdan You, Jiajia Yu, Weiguang Kong, Chunyan Zhang, Jinjin Bai, Wenguang Li, Ting Li
A C–H silylation of azauracils was developed via the combination of organic photoredox and hydrogen atom transfer (HAT) catalysis. Using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as the photocatalyst, quinuclidine as the HAT catalyst, and silanes as the silyl radical sources, a variety of silylated azauracils were synthesized in 43-87% yields. Moreover, pyrazinone, cinnolinone, and
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Electrochemically Promoted Skeleton Transformation of 2,1-Benzisoxazoles to Alkyl Sulfones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-11 Yun-Qi Wu, Sai-Yan Ren, Yu Zhu, Fei-Hu Cui, Ying-ming Pan, Hai-Tao Tang
Abstract. This study developed an electrochemically promoted skeleton transformation reaction of 2,1-benzisoxazoles to synthesize alkyl sulfones. The synthesis of alkyl sulfone products in 68%-93% yields by using 2,1-benzisoxazole and sulfonate as substrates, and acetonitrile and water were employed as solvents. Mechanism study shows that this reaction work involving the ring opening, the removal of
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Construction of Fused Azacyclic Systems via Cascade Cyclizations of Vinyl Sulfonium Salts Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-11 Yannan Zhu, Wei Wang, Shanshan Guo, Xinxin Ye, Bo Fang, Gang Qi
In this work, cascade cyclizations of vinyl sulfonium salts with either indolyl chalcones or ortho-amino trifluoroacetophenones are described. This protocol enables the assembly of fused 2,3-dihyro-1H-pyrrolo[1,2-a]indoles and fused tetrahydroquinolines containing a CF3-substituted tetrasubstituted carbon stereocenters.
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Microwave-Assisted Rhodium (III)-Catalyzed [3+3] Annulation of 2-Benzyl-2H-indazole-6-carboxylic Acids with Iodonium Ylides: A Regioselective Synthesis of Indazole-Fused Chromenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-10 Hong Ren Chen, Indrajeet Barve, Hung-Sheng Hsieh, Ganesh Pawar, Kuan-Miao Liu, Chung-Ming SUN
Abstract: A Rh (III)-catalyzed redox-neutral C-H activation/ [3+3] cyclization of 2-benzyl-2H-indazole-6-carboxylic acids with iodonium ylides under microwave irradiation for the synthesis of indazole-fused chromenes has been reported. The critical feature of this method is that the C-H activation of the C7-H bond of 2-benzyl-2H-indazole-6-carboxylic acid proceeds with regioselectivity in the presence
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Synthesis of 3,5-Dialkoxy-1,2-dioxolanes by Alkoxyperoxidation of 1,3-Diketones with Hydrogen Peroxide and Alcohols Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-10 Peter Radulov, Ksenia Skokova, Viktoria Dmitrieva, Dmitri Fomenkov, Igor Krylov, Alexey Ilovaisky, Ivan Yaremenko, Alexander Terent'ev
A three-component reaction of 1,3-diketones with H2O2 and alcohols was discovered. 3,5-Dialkoxy-1,2-dioxolanes are formed in yield ranging from 13% to 83% using an excess of acids such as H2SO4, MeHSO3, p-TsOH·H2O or BF3·Et2O. This reaction proceeds with the formation of 3,5-dialkoxy-1,2-dioxolanes despite the diversity of possible reaction pathways leading to different types of peroxides, oligomers
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Gold(III) Catalysis in Ionic Liquids: The Case Study of Coumarin Synthesis Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-10 Francesco Ravera, Marte Sofie Martinsen Holmsen, Paolo Sgarbossa, Didier Bourissou, ANDREA BIFFIS
Well-defined (P,C)-cyclometalated Au(III) complexes proved to be able to catalyze the synthesis of coumarins by intramolecular hydroarylation of a broad range of aryl propiolates under mild and practical conditions (0.1-2 mol% catalyst, 25-40°C, 1-24 hours). Use of an ionic liquid as reaction solvent allowed to drastically decrease the amount of Brönsted acid used to unlock the catalyst regeneration
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Iron-N,N,N’,N’-Tetramethylethylenediamine-Catalyzed Selective Substitution of Functionalized Diene and Triene Monoepoxides with Aliphatic Grignard Reagents Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-09 Shoma Kobayashi, Kazuma Abe, Takeshi Hata
When γ,δ-epoxy-α,β-unsaturated esters were treated with 3 equiv. of aliphatic Grignard reagents in the presence of 10 and 20 mol% of FeCl2 and N,N,N’,N’-tetramethylethylenediamine (TMEDA), regio- and stereoselective substitution of the epoxide moiety with the aliphatic Grignard reagent occurred to give exclusively δ-hydroxy-γ-alkyl-α,β-unsaturated esters in high yields. In addition, γ,δ-epoxy-α,β,ε
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Hypervalent iodine-mediated regioselective dearomatization of non-activated arenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-09 Yang Wang, Ji-Chen Yin, Yu-Wei Zhang, Yuzhe Zhang, Feng Shi
The dearomatizations of non-activated arenes, particularly those under mild reaction conditions, are highly desired transformations in organic synthesis due to their power in converting flat aromatic rings into three-dimensional frameworks. Although hypervalent iodine (HVI)-mediated dearomatization of phenol derivatives has developed rapidly, HVI-mediated dearomatization of non-activated arenes remains
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Ruthenium (II)-Catalysed Regioselective C6 Alkylation of Indoles with Maleimides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-09 Pankaj Jadhav, Sudam Dawande
Ruthenium (II)-catalysed regioselective C6 alkylation of indole-7-carboxamides with maleimide has been described. Electronically diverse maleimides reacted with various indoles to furnish corresponding C6 substituted succinimide derivatives of indoles with 46-89% yields. The reaction shows broad functional group tolerance. The synthetic utility of the reaction has been demonstrated through the conversion
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Electrochemical Oxidative Functionalization of Pyrazolin-5-ones: Access to 4-Quinoxalinone-Substituted Pyrazoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-09 Shuai Zhang, Zhihua Zhang, Changsheng Qin, Meiqian Hu, Jingfang Wang, Fanghua Ji, Guangbin Jiang
A strategy for the preparation of 4-quinoxalinone-substituted pyrazole derivatives by electrochemical functionalization of pyrazolin-5-ones is reported. Quinoxalinones, possessing significant biological activities, serve as aryl sources and participate in the transformation under electrochemical conditions without the necessity of adding extra oxidants and catalysts. This method features one-pot synthesis
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Magnesium and Calcium Bisguanidinates: Catalytic Activity in the Hydroboration of Unsaturated Molecules Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-06 Carlos Ginés, Blanca Parra-Cadenas, Rafael Fernández-Galán, Daniel García-Vivó, David Elorriaga, Alberto Ramos, FERNANDO Carrillo-Hermosilla
The role of ligands in catalytically active metal complexes can be crucial. Herein, we present a study on the synthesis and catalytic behavior of alkaline earth bisguanidinato complexes. The reactivity of trisubstituted guanidines, specifically (iPrHN)2CNR (R= Ph, 2-Ph2PC6H4, 2-MeSC6H4), towards magnesium and calcium alkyls or amides was explored. All the compounds were found to be very active in the
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Cs2CO3-Mediated Tandem Dimerizative (3+3) Cyclocondensation of 1,3-Acetonedicarboxylates. One-pot Synthesis of 2,4,6-Trialkoxy and Triaryloxybenzoates Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-05 Meng-Yang Chang, Chin-Huey Ho
In this study, Cs2CO3-mediated one-pot tandem dimerization/(3+3) cyclocondensation of 1,3-acetonedicarboxylates followed by substitution of alkyl or aryl halides was developed to construct functionalized 2,4,6-trialkoxy and triaryloxybenzoates. In the effective reaction, the core benzene system was formed in single-step process under open-vessel conditions. A plausible mechanism for this reaction is
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Hydrogen Bonding Interaction Enabled Ru(III)-Catalyzed Synthesis of (Multi)-Substituted Pyridines Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-04 Santana Chakraborty, Rina Sikari, Subhajit Chakraborty, Manisha Sharma, Paula Brandão, Nanda Paul
Herein, we report a cost-effective synthesis of various multi-substituted pyridine derivatives, especially 2-aryl pyridines, using secondary alcohols and 1,3-diol as the primary feedstock with ammonium acetate serving as nitrogen donor, catalyzed by a new well-defined singlet mono-radical Ru(III)-catalyst featuring a cyclopentadienyl group, one PPh3, and a redox-active scaffold ‒N1-(2-aminophenyl)benzene-1
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Asymmetric Addition of Allomaltol to Chalcones and Bis(arylidene)acetones: En Route to Chiral Drugs Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-04 Ruslan A. Kovalevsky, Alexander S. Kucherenko, Sergei G. Zlotin
The synthesis of enantiomerically enriched γ-oxobutiric acid and succinic acid derivatives based on asymmetric conjugate addition of allomaltol to chalcones or bis(arylidene)acetones in the presence of readily available and recoverable C2-symmetric tertiary amine-squaramide organocatalyst has been developed. Ru(III)-catalyzed oxidative transformation of pyran-4-ones bearing the α,β-enone unit to enantiomerically
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Enantioselective Synthesis of Planar Chiral Ferrocene Triflones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-04 Min Wen, William Erb, Florence Mongin, Jean-Pierre HURVOIS, Marielle Blot, Thierry Roisnel, Yury Halauko, Vadim Matulis, Yuta Koike, Yu Kitazawa, Mutsumi Kimura, Masanobu Uchiyama
A multi-gram scale synthesis of ferrocenetriflone was optimised from ferrocenesulfonyl fluoride and Me3SiCF3 (Ruppert reagent). Enantioselective deprotolithiations were then carried out using alkyllithiums in the presence of catalytic (+)-sparteine to afford 2-substituted ferrocene triflones with ee up to 84%. The use of chiral lithium amides in the presence of in situ traps was also optimised and
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Corrigendum: Mechanistic Insights on the Enantioselective (4+3) cycloaddition between Oxyallylcations and Furans Catalyzed by BINOL-based Phosphoramides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-02
In the research article “Mechanistic Insights on the Enantioselective (4+3) cycloaddition between Oxyallylcations and Furans Catalyzed by BINOL-based Phosphoramides” by Manuel Pedrón, Laura Villar, Uxue Uria, Liher Prieto, Tomas Tejero, Pedro Merino and Jose L. Vicario, in Issue 4, 2024, pp 916–924 (Adv. Synth. Catal. 2024, 366, 916–924, DOI: 10.1002/adsc.202301188), there is an error in the transcription
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Yb(OTf)3-Catalyzed C=C Bond Cleavage-Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-02 Zi-Li Liu, Chi-Fan Zhu, Yin-Ping Liu, Ke Chen, Qiuyun Li, Shu-Liang Wang, Wen-Juan Hao, Bo Jiang
A Yb(OTf)3-catalyzed [2 + 2] cycloaddition /retro-electrocyclization (CA-RE)/ bicyclization of 1-(2-aminoarylaklynyl)-naphthalen-2-ols and 3-ylideneoxindoles is reported, enabling a direct C=C bond cleavage-reassembly process to regioselectively synthesize a variety of quinoline-tethered benzo[5,6]chromeno[2,3-b]indoles in 31-84% yields. Exchanging the amino group for the hydroxyl group in the arylalkynyl
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Ru(II)-Catalyzed Weak Chelation-Assisted Regioselective C4−H Aminomethyl Alkenylation of Indole Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-02 Raziullah Khan, Mohit Kumar, Anushka Rastogi, Ashfaq Ahmad, Dipankar Koley
A Ruthenium catalyzed C4- aminomethyl alkenylation of indoles using substituted propargylamine as an alkenylating agent and pivaloyl as a weak chelating group has been demonstrated. A variety of substituted indoles and propargylamines furnished the desired product in good yields. Control experiments indicate that the C−H cleavage step is reversible and suggest the possibility of a base-assisted internal
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Oxidation State and Halogen Influence on the NHC-Gold-Halide-Catalyzed Cyclization of Propargylic Amides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-02 Nicola Sargentoni, Rossana Galassi, Lorenzo Luciani, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi
The homogeneously catalyzed cycloisomerization reaction of propargylic amides was tested as benchmark reaction for two homologous series of Au(I) and Au(III) complexes with NHC ligands. This reaction is known to afford either aromatic oxazoles or dihydrooxazoles, depending on the oxidation state of the applied gold catalysts. For this purpose, symmetric and unsymmetric NHC ligands with mixed alkyl
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Three-Component Synthesis of Substituted Azepines by Gold/Magnesium Orthogonal-Relay Catalysis Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-09-01 Shuto Kosuge, Yoshihiro Kiraku, Kiyoshi Tsuge, Kenji SUGIMOTO, Yuji Matsuya
A three-component one-pot synthesis of substituted azepines was realized by gold/magnesium orthogonal relay catalysis. The one-pot synthesis involves simply mixing and heating propiolates, imines, and activated cyclopropanes to initiate a gold-catalyzed aza-enyne metathesis between propiolates and imines, followed by a magnesium-catalyzed [4+3] cycloaddition reaction of the resultant 1-azabutadienes
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PTC in the polyenolate-mediated [10+2]-cycloaddition for the synthesis of α,α-disubstituted amino acid precursors Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-30 Joanna Dybowska, Artur Przydacz, Anna Skrzyńska, Łukasz Albrecht
Abstract. The manuscript describes a formal [10+2] higher-order cycloaddition between 2-benzylideneindan-1-ones and α-alkilidene azlactones as higherene precursors and higherenofiles respectively. The reaction is realized under Brønsted-base catalysis utilizing the phase transfer catalysis approach. The key intermediate is an isobenzofulvene-derived polyenolate which acts as a 10-electron component
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Tandem Electrochemical Redox/Condensation Reaction between 2-Amino Nitrobenzenes and Aliphatic Alcohols: An Approach to Benzimidazoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-30 Shuyong Song, Chengcai Xia, Zenghui Zhang, Wenjing Yang, Changji Liu
Tandem reactions via electrocatalytic annulations have emerged as an effective strategy for the construction of heterocycles. Herein, a two-component electrochemical annulation via sequential reduction, oxidation, and condensation steps to synthesize valuable benzimidazoles motifs is reported. This reaction, which utilizes electricity as both the oxidants and reductants, tolerates a broad range of
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Enantiocomplementary Synthesis of Tetrahydrofurans by Engineered Halohydrin Dehalogenases Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-30 Yujing Hu, Wenjing Wang, Mingye Zhao, Jie Chen, Shuyang Kong, Ning Zhu, Zheng Fang, Yongzhen Peng, Qi Wu, Kai Guo
Chiral tetrahydrofurans are prevalent structural motifs in biologically active compounds, approved drugs and natural products, but relevant enantiocomplementary synthesis remains underdeveloped. In this study, wild type halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, was first discovered to enable the intramolecular substitution of δ-halohydrins for the formation of tetrahydrofurans
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Molybdenum-Catalyzed Intramolecular Deoxygenative Annulation of 2-Acylazobenzenes to Access N2,C3-Disubstituted 2H-indazoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-29 Haoke Chu, Quanyun Liu, Mei-Hua Shen, Hua-Dong Xu
A molybdenum-catalyzed synthesis of N2,C3-disubstituted 2H-indazoles from readily available 2-acylazobenzenes via deoxygenation of C=O and annulation has been described. The non-noble metal catalytic system has good tolerance of functional groups, and various N2,C3-disubstituted 2H-indazoles have been constructed in 24% to 99% yield. This reaction is easy to scale-up and has shown its applications
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Exploring the Substrate Scope and Catalytic Promiscuity of Nitroreductase-like Enzymes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-29 Alex Prats Luján, Mohammad Faizan Bhat, Saravanan Thangavelu, Gerrit Poelarends
Flavin-dependent nitroreductases are gaining attention as biocatalysts for the synthesis of pharmaceutically active compounds and their precursors. Here, we examined a panel of nitroreductase-like flavoenzymes for their reductase activity towards a wide variety of aromatic and aliphatic nitro compounds, nitroolefins, and α,β-unsaturated carbonyl compounds. Several of these flavoenzymes displayed high
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Visible Light-Driven Difluoroalkoxylation of Imidazopyridines using N-Fluorobenzenesulfonimide as Fluorinating Agent Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-29 Amol Gadekar, Sonam *, Vikki N Shinde, Bhawani *, Krishnan Rangan, Anil Kumar
A visible-light-promoted site-selective difluoroalkoxylation of imidazo[1,2-a]pyridines has been achieved using N-fluorobenzenesulfonimide (NFSI) as a fluorinating agent. This practical reaction has a wide range of substrate scope for both imidazo[1,2-a]pyridines and alcohols to give 3,3-difluoro-2-alkoxy-2-arylimidazo[1,2-a]pyridines in 65-93% yields. The reaction proceeded at room temperature, showed
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Visible Light Mediated Difluoroalkylation of Alkenes Using Mercaptobenzothiazole-Derived Sulfide Reagent Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-28 Artem Sorokin, Vitalij Levin, Alexander D. Dilman
A method for the reductive difluoromethylation of alkenes with 2-difluoromethylthio(benzothiazole) under photocatalytic conditions is described. The reaction involves the generation of the difluoromethyl radical by means of trimethyltriazinane, which serves as a precursor for the strongly reducing cyclic diaminoalkyl radical.
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Palladium-Catalyzed Directing-group-mediated γ-C(sp3)-H Glycosylation for Synthesis of C-Alkyl Glycosides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-28 Qiuyu Zhong, Changyu Yu, Jinlin Wang, Jiang Wang, Kaixian Chen, Hong Liu, Wenhao Dai
C-alkyl glycosides play a crucial role in various bioactive compounds. However, the synthesis of C-alkyl glycosides poses significant challenges, particularly through C(sp3)-H glycosylation. Here, we report a set of reactions for constructing C-alkyl glycosides through directing-group-mediated functionalization of unactivated γ-C(sp3)-H bonds under mild conditions. Those reactions not only achieve
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One-Pot Reactions of Ynones with Isothiocyanates for Accessing 2-Aminothiophenone and Indole-Fused/Indole-Substituted Thiophenone Derivatives Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-28 Zefeng Jin, Cuiying Li, Guodong Shen, Honglan Kang, Xin Lv
A copper or silver-catalyzed cascade addition/5-exo-dig cyclization/isomerization reaction of isothiocyanate with ynone has been developed. This strategy enables the synthesis of a variety of (Z)-2-ylidene-5-aminothiophen-3-one derivatives with diverse substitutions in a single vessel. The method is featured with pot-economy and high regio- and Z-selectivity. Several biologically active molecules could
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Fluorine Chemistry: An Outlook to the Future Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-28 Véronique Gouverneur
Véronique Gouverneur Fluorine chemistry has had a long history with key milestones since the 16th century including the first use of fluorite in smelting, the synthesis of hydrogen fluoride first reported by Carl W. Scheele in 1771, and the production of elemental fluorine by Henri Moissan in 1886. Moissan was awarded the Nobel Prize in Chemistry twenty years later for this achievement. Considering
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1-Alkynylphosphorus Compounds in Organic Synthesis,2010-2024 Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-08-28 Long Chen, Hai-Liang Ni, Zhong Wen, Huan-Zhu Xue
Since the review of Yorimitsu and Oshima in 2010, the past 15 years have witnessed significant progresses in the application of 1-alkynylphosphorus compounds in organic synthesis. Owing to the reactive carbon-carbon triple bond in association with the electron-withdrawing phosphoryl group, they easily undergo transition metal-catalyzed nucleophilic addition reactions at the β-position with carbon-