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Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-25 Jong-Un Park, Ju Hyun Kim
Chiral N‐heterocyclic compounds are key structures in natural compounds and pharmaceuticals, and they serve as essential building blocks of functional materials. Catalytic asymmetric cycloaddition reactions represent one of the most efficient synthetic strategies for constructing optically active heterocycles. Cyclic sulfamidate imines have recently come to be extensively studied and widely utilized
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Recent Advances on Direct Phosphorothiolation Reactions Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Haifa Zheng, Ju Peng, Xiang Liu, Ping Zhao
Organophosphorothioates are organic molecules containing sulfur and phosphorus, with significant biological activity and physicochemical properties, widely used in organic synthesis, medicinal chemistry, and the agrochemical industry. In particular, many phosphorothioates display a variety of biological activities, such as antifungal, antibacterial, anti‐parasite, anticancer, and so on. Traditionally
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Catalytic Deoxygenative Transformation of Ketoacids/Esters for the Synthesis of Coumarin, Benzofuranone, and Dihydrobenzo[b]oxepin‐2(3H)‐one Derivatives. Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Naveen Yadav, Jabir Khan, Chinmoy Hazra
We disclose herein a triflic acid and silane‐promoted reductive deoxygenative transformation of ketoacid/esters for the divergent synthesis of different‐sized lactones, which hold substantial significance in pharmaceutical and natural product chemistry. Owing to the simple reaction conditions and setup, this protocol features broad substrate generality, scalability, and good functional group tolerance
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Rapid (Deuterio)difluoromethylation of Heteroatoms using R‐22 Gas: A Demonstration of Flow Chemistry in Suppressing Intrinsic Reaction Pathways Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Hon Cheung Leung, Tsz Chun Lee, Wing-Tak Wong, Wai Chung Fu
The exploration and use of deuteriodifluoromethyl heteroatom groups (X‐CF2D) has been limited by persistent challenges, including the unavailability of CF2D precursor reagents, as well as safety, scalability, and environmental concerns associated with conventional batch‐mode syntheses. In this study, we report the use of atom‐efficient and cost‐effective R‐22 gas (ClCF2H) in continuous flow for the
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A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Upasana Deka, Arup Jyoti Das, Swapnil Kumar Nath, Dr Sajal Kumar Das
Reported herein is a method for the construction of azepino[1,2‐a]indoles via an intramolecular aldehyde–alkyne metathesis of 1‐(5‐aryl‐4‐pentynyl)indole‐2‐carbaldehydes. This Sc(OTf)3‐catalyzed reaction has several remarkable features, such as ready accessibility of the starting materials, broad substrate scope, operational simplicity, and high yields. The practicality of the process and the synthetic
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Oxidative photochemical cyclisations to access spiroketals Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Jonathan Trevorrow, Nhlanhla Sibanda, Anne O'Kearney-McMullan, Lucie Miller-Potucka, Adrian Dobbs
The spiroketal moiety is an important substructure within many biological natural products. One method to access them is via the oxidative cyclisation of a pendant hydroxyl group on to a pre‐formed pyran. However applications of this methodology have been severely limited by requiring the use of toxic and powerful oxidants, such as lead (IV) tetraacetate or mercuric oxide. Herein we report a novel
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Benzene‐1,3‐disulfonyl fluoride and Benzene‐1,3,5‐trisulfonyl fluoride: Low‐Cost, Stable, and Selective Reagents for SuFEx‐Driven Deoxyazidation Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Dharmendra Vishwakarma, John Edward Moses
The development of synthetic methods for the synthesis of organic azides is highly important, given their critical role in advancing click chemistry over the last twenty years. We report a reagent‐economical, reliable, and scalable synthesis of alkyl azides from primary and secondary alcohols. This robust click method capitalizes on the synergistic interaction between Sulfur Fluoride Exchange (SuFEx)
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Bunte Salts for Electrochemical Deuteroalkylthiolation of Heteroarenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Ruhan Lu, Qisheng Tao, Qing Qian, Bo Li, Yuhuan Zhang, Yongyuan Gao
This study presents a strategy for the electrochemical deuteroalkylthiolation of heteroarenes, using Bunte salt as a deuterium‐alkylthio source. This reaction occurs in an undivided cell without the need for catalysts, oxidants, or electrolytes, yielding a variety of deuteroalkylthiolated heteroarenes.
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Advances in α‐Hydroxylation of β‐Dicarbonyl Compounds Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Shuai Peng, Fangyao Su, Shuting Yin, baoguo sun, Hongyu Tian, Sen Liang
The α‐hydroxy‐β‐dicarbonyl motif is essential in many biologically active compounds, sparking significant interest in their synthesis. This review comprehensively examines the advancements in the α‐hydroxylation of β‐dicarbonyl compounds, systematically categorizing the methods based on the types of oxidants employed and highlighting advances in asymmetric α‐hydroxylation. It evaluates the substrate
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Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 Shuoshuo Zhang, Lingzhi Xu, Xuemin Li, Zhifang Yang, Haofeng Shi, Yadong Li, Yunfei Du
A class of cyclohexenone(aryl)iodonium salts was readily prepared from 2‐iodocyclohexenones and arenes under mild conditions. This novel series of hypervalent iodonium building blocks exhibits dual characteristics of hyperiodonium salts and α,β‐unsaturated cyclic ketones, enabling access to intricate aza‐heterocycles. The reaction of these cyclohexenone(aryl)iodonium salts with arylamines and benzene
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Merging Organolithium Chemistry and Stereoselective Biocatalysis: Transformation of Aromatic Nitriles into Chiral Alcohols. Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-23 N. Ríos‐Lombardía, G. Morís‐Menéndez, I. Lavandera, V. Gotor‐Fernández, J. García‐Álvarez
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Synthesis, Characterization and Biological Evaluation of 3‐Oxo‐pyrimido[1,2‐b]indazoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-20 Xinyu Zhang, Xuan Zhao, Die Wu, Jingsa Zhang, Yilu Shou, Xingya Wang, Yongmin Ma, Bihong Zhu
The synthesis of substituted 3‐oxo‐pyrimido[1,2‐b]indazoles from 3‐aminoindazoles and ketones has been established. It involves one molecule of 3‐aminoindazoles and two molecules of ketones via a [3+2+1] three‐component annulation process. 3‐Oxo‐pyrimido[1,2‐b]indazoles exhibit strong yellow fluorescence in various solvents. A wide range of products have anti‐oxidant activities. Cytotoxicity studies
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Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐heterocycles with N‐methoxyindoleamides and Isoxazolones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-20 Shang-Shi Zhang, Dan-Ting Shen, Wen-Xuan Zou, Shao-Yong Chen, Lin Xiao, Qiong Hu, Jia-Lin Song, Xu-Ge Liu
A method for synthesizing pyrimido[1,2‐a]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C‐H activation/annulation strategy employing N‐methoxyindoleamides and isoxazolones is developed. Also, a framework of 3‐methoxy‐2,3‐dihydro‐[1,3,5]triazino[1,2‐a]indole‐4,10‐dione was successfully synthesized via a Cp*Rh‐catalyzed C‐H activation/annulation/oxidation reaction between N‐(methyloxy)‐1
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Cu‐catalyzed Formal Addition of Aliphatic C(sp3)–H Bonds to Alkenes via Phenyl Radical Involved Intermolecular HAT Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Peizhi Bai, Xin Zhang, Qinshuang Su, Tiebo Xiao, Yubo Jiang, Guoying Zhang, Yinjun Xie, Guiping Qin
A copper catalyzed aerobic formal addition of aliphatic C(sp3)–H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a good HAT reagent precursor but also as an excellent hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of the aliphatic C(sp3)–H bonds to alkenes utilizing
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Dearomative 1,2‐(Deutero)Hydrotrifluoromethylation of Chromium‐Bound Arenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Cheng-Jie Wu, Xu Jiang, Jia-Yi Qiu, Ming-Yang Wang, Wei Li
Dearomative trifluoromethylation of arenes provides an ideal method for constructing CF3‐containing three‐dimensional architectures which are of increasing interest in drug discovery. However, such transformation is rare and challenging because of the inherently low reactivity of arene π‐systems and selectivity issues. Herein, we disclose a general dearomative 1,2‐hydrotrifluoromethylation of (hetero)arenes
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Synthesis of Acyl Halides from Carboxylic Acid Thioesters for Synthesis of Ketones, Esters, Amides and Peptides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Shuji Nagano, Keiji Maruoka
A synthesis of acyl halides from the corresponding carboxylic acid thioesters was achieved using commercially available Selectfluor or NCS, and the acyl fluoride or chloride intermediates were transformed to the corresponding esters, amides, and several carbon‐carbon bond formation products. This approach can be applied to the peptide synthesis from functionalized amino acid thioesters.
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Neighboring π‐Coordination in Palladium Catalyzed [4+4] Cycloaddition of γ‐Methylidene‐δ‐Valerolactones with Divinylketones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Xiaoying Wu, Wei Feng, Jiayi Zhao, Daoshan Yang, Ran Song, Wen Si, Jian Lv
A palladium‐catalyzed [4+4] cycloaddition of aryl‐substituted γ‐methylidene‐δ‐valerolactones (GMDVs) with divinylke‐tones (DVKs) was developed, providing an approach to access various mono‐cyclic tetrahydro‐2H‐oxocines with diverse substituents in up to 95% yields and >20:1 dr. This reaction was facilitated by anchoring olefin (C=C) at the α‐position of carbonyls.
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Organophotocatalyzed C‐Si Bond Fragmentation Using Silyl Ethers as Radical Precursors Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Adrian Luguera Ruiz, Valentina Benazzi, Federico Tucci, Francesca Rizzo, Daniele Merli, Stefano Protti, Maurizio Fagnoni
In this work, silyl ethers of phenols and alcohols have been successfully prepared and tested as neutral carbon (silicon) centered radical precursors. The organocophotocatalyzed oxidation (by the Fukuzumi catalyst) of these ethers caused the cleavage of a C‐Si (or a Si‐Si) bond for the release of the desired radical to be used for the forging of C(sp3)‐C(sp3) (or C(sp3)‐Si) bonds via a Giese reaction
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Metal‐free photocyclization/oxidation cascade constructing quinoline‐2‐ones and tetrahydrocarbazolones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-19 Yanke Hao, He Huang
We reported a one‐pot photocyclization/ oxidation cascade of N‐aryl acrylamides to afford quinoline‐2‐ones. Thioxanthone was used as a bifunctional energy transfer agent to mediate both photocyclization and generation of singlet oxygen, the latter facilitates the dehydrogenation of dihydroquinoline‐2‐one intermediate. This cascade strategy also supports the 5‐endo‐trig cyclization to synthesize te
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Total Synthesis of (‐)‐Daphenylline by Gold‐Catalyzed Intramolecular Dearomatization Reaction of Methoxynaphthalene Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-18 Meng-Yue Cao, Qing-Xiu Gu, Jinguo Long, Xianjie Fang, Hai-Hua Lu
Daphenylline, a structurally unique triterpenoid Daphniphyllum alkaloid, has attracted considerable attention from the synthetic community since its isolation. Herein, we delineate an enantioselective total synthesis of (‐)‐daphenylline, which is based on a gold‐catalyzed dearomatization reaction of β‐methoxynaphthalene. Other features include installation of the initial chiral stereocenter via an
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Enzyme Cascade with Four Enzymes in One Pot for the Synthesis of L‐Phosphinothricin Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-18 jianmiao xu, Zhijie Xi, Keji Keji Zhao, Chenxiang He, Feng Cheng, Ya-Ping Xue, Yu-Guo Zheng
The biocatalytic oxidative deamination‐ reductive amination process for the production of L‐phosphinothricin (L‐PPT) from D,L‐phosphinothricin (D,L‐PPT) is a green and environmentally friendly approach with significant development potential. In this study, the adopted technological route involves the oxidative deamination of the D‐PPT component in D,L‐PPT to 2‐oxo‐4‐(hydroxymethylphosphinyl)butanoic
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One‐Pot Synthesis of 3‐Hydroxy‐1H‐Pyrrolo[3,4‐b]quinolin‐1‐one via Enaminamides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-16 Xi Shen, Zhi-Cheng Yu, You Zhou, Yandong Wu, Anxin Wu
A multicomponent cascade cyclization reaction using aryl methyl ketones, aryl amines, and enaminamide reagents to construct 3‐hydroxy‐1H‐pyrrolo[3,4‐b]quinolin‐1‐one skeleton with good substrate compatibility (50 examples) has been reported. The one‐pot, metal‐free process formed two C‐C bonds, two C‐N bonds, and a tetrasubstituted carbon stereocenter containing a hydroxyl group. The reaction enabled
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An Acid Catalyzed Alkynyl‐Prins Cyclization–Rearrangement Cascade of 2‐(Alkynol)benzoates: An Approach to 3‐Alkyl‐[n,5]‐oxaspirophthalides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-13 Beeraiah Baire, Surabhi Mishra
The oxaspiro‐phthalides ([n,5]‐oxaspirobenzalactones) bearing a phthalide spirofused to a cyclic‐ether of various sizes are frameworks found in bioactive natural products. The discovery and development of an alkynyl‐Prins cyclization based, strategy for the construction of structurally interesting, medicinally useful [5,5]‐ [6,5]‐, and [7,5]‐oxaspirophthalides is reported in this manuscript. Our strategy
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Palladium‐Catalyzed Bicyclization of 1‐(2,2‐Dibromovinyl)‐2‐Alkenylbenzene with Allenyl Malonates Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-12 ping xin zhou, Yang Liu, Cui-Tian Wang, Kexin Li, Feng Ren, Xinqiang Tan, Yong-Min Liang
Palladium‐catalyzed bicyclization of 1‐(2,2‐dibromovinyl)‐2‐alkenylbenzene with allenyl malonates has been achieved to afford a series of bicyclic compounds. The protocol involves intermolecular carbopalladation of allenes/cyclization/internal Heck reaction. Three C‐C bonds and two rings are formed in one step.
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Oxidative Synthesis of 2,5‐Diarylphenanthro[9,10‐c]thiophenes and Their Aerobic Photoconversion to 9,10‐Diaroylphenanthrenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-12 Sankarrao Mahanthi, Sudhakar Maddala, Venkatakrishnan Parthasarathy
Our study introduces a streamlined oxidative method for synthesizing 1,3‐diarylphenanthro[9,10‐c]thiophenes, and their subsequent oxidative cleavage to yield 9,10‐diaroylphenanthrenes. Harnessing an optimized aerobic photochemical transformation, we showcase broad substrate scope and tolerance to various photosensitive functional groups. Our mechanistic investigations unveil the pivotal role of singlet
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K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole From 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael addition/C–Cl bond cleavage/deformylation as Key Fragmentation Sequences Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-12 Biswajit Maji, Aniruddh Pratap, Pushpendra Mani Shukla, Santanab Giri
Here we report a transition metal– and oxidant–free annulation cascade method for the synthesis of chromeno–isoxazoles. The annulation reaction involves easily accessible starting materials, 3‐nitro‐2H‐chromene and α‐chloro aldehyde, yielding the structurally intriguing framework, chromeno[3,4‐c]isoxazoles employed by tripotassium phosphate as a base. The isoxazole ring construction over the 2H–chromene
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Cyclization Through Dual C(sp3)–H Functionalization Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-11 Masoud Sadeghi
C(sp3)–H functionalization methods have been widely employed in many organic transformations such as cyclization reactions, heterocycle synthesis, cross‐coupling protocols, and photochemical transformations. Among these transformations, cyclization reaction through C(sp3)–H functionalization offers a direct route to convert simple linear substrates to complex products. There are three modes of utilizing
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Redox‐Neutral Vicarious‐Type Nucleophilic Amination of Heterocyclic N‐Oxides with Organic Azides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-11 Jeonghyun Min, Sujin Min, Eunjae Chung, Kyeongwon Moon, Hyung Sik Kim, Taejoo Jeong, AMITAVA RAKSHIT, Pargat Singh, Jung Su Park, In Su Kim
Site‐selective amination of N‐heterocycles is an interesting topic in organic synthesis and drug discovery. We herein present a method for the vicarious‐type nucleophilic amination of azine N‐oxides and cyclic iminoamides using iminyl anions, readily generated from organic azides under basic conditions. The plausible reaction mechanism involving nucleophilic aromatic substitution by iminyl anions is
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Visible Light‐Induced Copper‐Catalyzed Alkylation/exo‐Cyclization of 1,7‐Dienes with Sulfonium Salts to Access Sulfur‐Containing Polycyclic Compounds Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-09 Xin-Qian Liu, Jian-Hong Fan, Kewen Tang, Long-Jin Zhong, Yu Liu
A direct visible‐light‐promoted radical‐triggered tandem cyclization of 1,7‐diene systems with cyclic sulfonium salts by using copper(I)‐based complexes as photoredox catalyst is developed. With this approach, a variety of sulfur‐containing polycyclic derivatives are prepared through alkylation/6‐exo‐trig cyclization/5‐exo‐trig cyclization of 1,7‐diene systems under mild conditions. In addition, the
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Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-06 Jun Pan, Yuting Feng, Leiyang Lv, Zhiping Li
A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides and HOOtBu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, the β‐peroxy‐phosphine oxides were selectively obtained with a catalytic amount of base, while the addition of acid led to the exclusive formation
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Nickel‐Catalyzed Enantioselective α‐Allylation of Cyclic Ketones with Allylic Alcohols Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-05 Neng-Quan Jiang, Ming-Ming Li, Li-Jun Xiao, Qi-Lin Zhou
Transition‐metal‐catalyzed asymmetric α‐allylation of ketones is a particularly useful tool for constructing stereocenters via C–C bond formation. However, this type of reaction often necessitated the use of activated ketones or pre‐prepared enol intermediates as substrates. In this study, we developed a nickel‐catalyzed α‐allylation of unactivated cycloketones with allylic alcohols to synthesize chiral
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Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-04 Predrag Jovanovic, Milos Jovanovic, Milos Petkovic, Milena Simic, Gordana Tasic, Marko Rodic, Srdjan Rakic, Filip Vlahovic, Vladimir Savic
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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 : 2024-07-04 Juan Carlos Pérez-Sánchez, Raquel Herrera, M. Concepción Gimeno
Another class of gold(I) redox‐switchable catalysts, incorporating ferrocenyl phosphane‐imines, enriches the existing library of gold(I) complexes. Our catalyst proves efficacy in gold(I)‐catalyzed cyclizations of furans and benzamides, exhibiting reversible “on‐off” switching. Furthermore, we explored the unconventional role of “Magic Blue”, commonly used as an oxidizing agent in various organic transformations
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1‐Oxa‐2,6‐diazaspiro[3.3]heptane as a New Potential Piperazine Bioisostere – Flow‐Assisted Preparation and Derivatisation by Strain‐Release of Azabicyclo[1.1.0]butanes Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-04 Elena Graziano, Philipp Natho, Michael Andresini, Fabrizio Mastrolorito, Iktedar Mahdi, Ernesto Mesto, Marco Colella, Leonardo Degennaro, Orazio Nicolotti, Renzo Luisi
The development of novel strained spiro heterocycles (SSHs) as bioisosteres for aromatic or non‐strained aliphatic rings is highly sought after for improving drug design. Their high molecular rigidity and predictable vectorization can enhance drug‐likeness, target selectivity and clinical success. Towards this goal, 1‐oxa‐2,6‐diazaspiro[3.3]heptane (ODASE) is reported as a novel potential SSH‐bioisostere
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Tandem Enantioselective Cycloaromatization/ Intramolecular Friedel–Crafts Desymmetrization of Cyclohexadienones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-04 Daniel Gaviña, Marta Durán, Lidia Prieto, Marcos Escolano, Santiago Díaz Oltra, Maria Sanchez-Rosello, Carlos del Pozo
An enantioselective tandem sequence that comprises a cycloaromatization process followed by an intramolecular desymmetrizing Friedel‐Crafts alkylation of functionalized cyclohexadienones has been accomplished. The process takes place in good yields (65‐95%), with excellent diastereoselectivity (>20:1) and enantiomeric ratios up to 90.5:9.5 in the presence of (R)‐BINOL‐derived N‐triflyl phosphoramides
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Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-04 Xiao Yu, Liqiang Hao, xian Liu, Shengkui Jin, Yiping Liu, Ya-Fei Ji
A one‐pot method has been developed for synthesizing diverse substituted 5‐aminotetrazoles via the electrochemically induced desulfurizative addition‐cyclization of thioureas with azidotrimethylsilane. This methodology enables the construction of C–N and N–N bonds under mild reaction conditions without transition metal catalysts or external oxidizing agents. The applicability of this approach is demonstrated
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Pd(II)‐Catalyzed Formal [5 + 2]‐Carbocyclization of ortho‐Aryl‐Substituted Arylaldehydes with Allylic Alcohols Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-04 Wei Zeng, Huanfeng Jiang, Chengjie Wang
A Pd(II)‐catalyzed formal [5+2] coupling‐cyclization of 2‐arylbenzaldehydes with allylic alcohols has been developed. The method provides an efficient approach to access diaryl‐fused cycloheptene skeletons via traceless α‐amino acid‐assisted Csp2‐H activation process.
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Functionalized α-Fluorinated Amines from Imines and Enol Ethers Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Dimitra Kyrko, Murat Saraç, Jing Hao, Pascal Retailleau, Sandrine Ongeri, Benoît Crousse
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Annulative Coupling of β‐Ketosulfoxonium Ylides and β‐Ketothioamides: Access to Thiazolines and Thiazolidin‐4‐ones Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Rahul Kumar Saini, Satyendra Pandey
A catalyst‐ and additive‐free one‐step protocol for synthesizing thiazolines and thiazolidin‐4‐ones, utilizing the annulative coupling between β‐ketosulfoxonium ylides and β‐ketothioamides has been described. The dual functionalization of β‐ketosulfoxonium ylides through S‐alkylation and intramolecular N‐cyclization leads to the generation of both C–S and C–N bonds. The developed synthetic methods
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Accessing 2‐(chalcogen)benzothiazoles via electrochemically mediated intermolecular cyclization of isocyanides with thiols or diselenides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Yi Zhang, Zu-Yu Mo, Xin-Yu Tang, Hai-Tao Tang, Ying-ming Pan, Kedi Yang, Yong-Lin Huang, Mu-Xue He
2‐(chalcogen)benzothiazoles are frequently used as core structures for the development of pharmaceutical agents. A mild strategy for the synthesis of 2‐(chalcogen)benzothiazoles under electrooxidative conditions using isocyanides, thiols or diselenides as substrates was developed. This protocol allows access to structurally diverse 2‐(chalcogen)benzothiazoles in good yields and with good functional
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Base‐Catalyzed Domino Isomerization/Oxidant‐Free Dehydrogenative Annulation of Allylic Alcohols: Scope, Mechanism, and Application Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Jia-Qi Li, Xiongyang Zhou, Xun Li, Cheng Le
A domino reaction comprising four consecutive steps based on the strategy of isomerization of allylic alcohols was developed. This base‐catalyzed protocol provided an approach for constructing polysubstituted quinolines without additional additives. A wide range of di‐ or trisubstituted γ‐aminoaryl allylic alcohols bearing alkyl or (hetero)aryl substituents were transformed to the structurally diverse
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Manganese Catalyzed Site‐Selective Hydroxymethylation to 2‐Pyridones and Isoquinolones via C‐H Activation Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Anushka Rastogi, Mohit Kumar, Manoj Kumar Gangwar, Dipankar Koley
Pyridine‐directed regioselective C‐H hydroxymethylation to pyridones and isoquinolones using para‐formaldehyde has been developed under manganese catalysis, offering a wide variety of hydroxymethylated products in 40‐85% yields. This operationally simple methodology proceeds in one step using an earth‐abundant first‐row transition metal‐catalyst without the generation of unwanted salt wastes. A mechanistic
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Radical Difunctionalization of Unsaturated Hydrocarbons Employing the Same Functional Reagent Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-03 Wen-Chan Tian, Nan-Nan Dai, Yue-Jiao Lu, Mu-Han Li, Yiping Ruan, Ting Li, Wen-Ting Wei
The radical difunctionalization of unsaturated hydrocarbons serves as an efficient means to rapidly construct molecular skeletons and synthesize‐highly valuable compounds. In this transformational process, diverse positions within unsaturated hydrocarbons are sequentially functionalized by a single radical precursor reagent, thereby achieving highly efficient and selective transformations that promote
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Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C‐P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-02 Dingsheng Cao, Jie-Ping Wan, Yunyun Liu
With an in situ C‐H iodination tactic, an applicable method for the synthesis of chromone‐3‐phosphonates has been developed with trialkyl/triaryl phosphites as the reaction partners of o‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists of cascade C‐H iodination, chromone annulation, and Arbuzov‐type C‐P cross coupling as major transformations. In addition to providing
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Formal Olefinic C−H Phosphinylation via Alkenyl Sulfonium Salts Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-02 Juan Ma, Jie Lin, Mingrui Li, Liandi Wang, Kaikai Wu, Yong-Gui Zhou, Zhengkun Yu
Formal olefinic C−P cross‐coupling between alkenyl sulfonium salts and secondary phosphine oxides and H‐phosphinates has been developed. A base enables construction of alkenyl C−P bonds as well as aliphatic C−P bonds at ambient temperature under an air atmosphere. This protocol provides an alternative access to multisubstituted alkenyl phosphine oxides and phosphinates in 40‐99% yields from functionalized
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Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-02 Leiqing Fu, Hongxiang Huang, Yingying Jiang, Xuan Liu, Huimin Chen, Jie-Ping Wan
A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e] isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54‐72% yields. Moreover, a plausible mechanism for this reaction was proposed based on several control experiments, deuterium exchange experiments, and previous reports
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Unconventional Ligand‐to‐Catalyst Ratio for the Distal C–C Bond Formation via C–H Activation and Chain‐Walking Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-02 King Hung Nigel Tang, Haluhi Takahashi, Ryo Tokutake, Takanori Shibata
A mechanism‐navigated enantioselective alkylation of an indole C2 C–H bond with an internal alkene was developed. Under the inharmonious ligand‐to‐metal catalyst ratio, a moderate enantiomeric ratio (er) was achieved with our original ligand. We propose that chain‐walking and bond formation are mechanistically independent, and suggest that hydridoiridium does not play a role in the chain‐walking process
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Nickel‐Catalyzed Regio‐ and Stereoselective Reductive Alkylative Cyclization of 1,6‐Enynes with Alkyl Bromides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-02 Yunxin Xing, Zhu Tian, Kun Shen
A nickel‐catalyzed reductive alkylative cyclization of 1,6‐enynes with alkyl bromides has been developed. This transformation avoids the use of stoichiometric organometallic reagents and introduces alkyl groups regio‐ and stereoselectively into the products. This method provides a platform for the synthesis of carbo‐ and heterocycles that are widely found in many natural products and biologically active
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Palladium-Catalyzed Sc(OTf)3/Cs2CO3-Assisted C−O Cross-Coupling of Vinylidenecyclopropane-Diesters with Phenolic Compounds Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-01 Xian-Hua Zhong, Yong-Jie Long, Yin Wei, Min Shi
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Front Cover Picture: Suzuki-Miyaura Reaction of Glycals with Base-Labile Protecting Groups as a New Route to Glycoporphyrins (Adv. Synth. Catal. 13/2024) Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-07-01 Bartosz Godlewski, Maciej Malinowski
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Regioselective and Diastereoselective Decarboxylative Allylic (Amino)Ketalization of Dihydropyranone Derivatives Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-28 Yingxi Lu, Xuelun Duan, Wangze Song, Wenfeng Jiang
It remains a challenge to achieve regioselectivity and stereoselectivity in the synthesis of dihydropyranone derivatives. Herein, an Ir/Pd‐catalyzed decarboxylative allylic (amino)ketalization was disclosed to prepare dihydropyranone derivatives in regio‐ and diastereoselectivities under mild conditions, resulting in O‐ and N‐allylative products. It provided a strategy for the post‐modifications of
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Nickel‐catalyzed reductive amidation of aryl sulfonium salts with isocyanates for amide synthesis via C‐S bond activation Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-28 Xue Chen, Meng-Ke Xu, Xuan-Qi Zhang, Chengping Miao, Xue-Qiang Chu, Weidong Rao, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
A nickel‐catalyzed reductive amidation of aryl sulfonium salts with isocyanates for amide synthesis via C‐S bond cleavage was developed. The reactions proceeded smoothly at ambient temperature in the presence of nickel catalyst and manganese metal in DMF to give a variety of amides in moderate to good yields with wide functional group tolerance.
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Iodine Mediated Annulation of Triethylamine, Aldehydes and 2‐Aminopyridines for the Synthesis of 3‐Formyl‐Imidazo[1,2‐a]pyridine Derivatives Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-28 Wenqing Zhang, Lihong Shen, Jun Zhang
With triethylamine as a synthon, an alternative method for the synthesis of 3‐formyl imidazo[1,2‐a]pyridines has been accomplished from aldehydes, and 2‐aminopyridines. The reaction proceeded via iodine‐catalyzed C−N bond cleavage of triethylamine, generation of α,β‐unsaturated aldehyde in situ, and oxidative cyclization with air as the oxygen source. This protocol may facilitate the synthesis of imidazo[1
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Photocatalytic α‐Difluoroalkoxyketones Synthesis via Radical Intermolecular Alkoxylation of Difluoroenol Silyl Ethers Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-27 Julien Paut, Simone Baldon, Elsa Anselmi, Luca Dell'Amico, Guillaume Dagousset, Emmanuel Magnier
. We present a new metal‐free photocatalytic approach for the synthesis of difluoroalkoxylated ketones. This strategy involves the generation of alkoxyl radicals from pyridinium salts upon the activity of a catalytic electron‐donor‐acceptor (EDA) complex. This mild process tolerates several functional groups and can be scaled up to gram scale. Diverse products manipulations accounts for the versatility
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Electrochemical α‐Functionalization of N‐Aryl‐Activated Tertiary Amines Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-27 Feijun Wang, Kevin J. Frankowski
Numerous appropriately substituted pyridyl or phenyl groups serve as a particularly advantageous activation motif for the electrochemical oxidation of amines. Such groups enable a general, mild method for the electrochemical α‐functionalization of tertiary amines across numerous activating groups and amine scaffolds. Notably, the method accommodates an unprecedented range of nucleophile classes, allowing
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Intramolecular Buchner reaction: experimental and theoretical comparison of the effect of the carbene substituent on the chemoselectivity. Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-26 Bich Tuyen Phung, Amira Medini, Pascale Maldivi, Jean-François Poisson, Bernard Bessières, BENJAMIN DARSES
The intramolecular Buchner reaction is a powerful transformation able to dearomatize benzenic rings. However, the competitive C–H insertion of the carbene moiety into benzylic positions still remains a limitation, and the reasons governing this uncomplete chemoselectivity are poorly understood. The carbene substitution, in particular, have been observed to influence strongly the selectivity, though
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Ligand‐free Pd‐catalyzed synthesis of PAHs via vinyl C‐H activation/decarboxylative cyclization sequence Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-26 Jie Sun, Long Yao, Fei Sun, Mingxia Wu, Yanfang Shang, Xin-Xing Wu
Herein, we describe a strategy for the synthesis of polycyclic aromatic hydrocarbons (PAHs) from readily available 2‐iodostyrenes and o‑halobenzoic acids through a ligand‐free palladium‐catalyzed cascade vinyl C‐H activation/decarboxylative cyclization. A vinyl‐coordinated five‐membered palladacycle was proposed as the key intermediate for this sequential process. Furthermore, Heptagon‐embedded aromatic
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Nucleophilic Cyanation of Enones and Imines with Formamide as the Cyano Source Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-26 Lei Luo, Hong Dai, Ming-Qing Yang, Luo Yang
A convenient and safe cyano source for the nucleophilic 1,4‐addition to enones and 1,2‐addition to imines has been developed, by generating the cyano unit in situ. via the TCT‐assisted dehydration of formamide. This protocol distinguishes itself by transition‐ metal/ligand free conditions, compatibility with 1,4‐/1,2‐addition, readily available substrates and versatile synthetic utilities of the cyanated
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Thermal‐Induced Synthesis of Cyclobute[b]indolines via Intramolecular Formal [2+2] Cycloaddition of Enamines and Triazole‐derived Ketenimines Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-25 Huan Luo, Han Wang, Wenzheng Zhang, Zefeng Xu, Shengguo Duan, Chuan-Ying Li
A de novo synthesis of cyclobutene‐fused indoline derivatives via thermally induced intramolecular cyclization was reported. This approach efficiently yields valuable high‐strained cyclobute[b]indolines in moderate to high yields and enables further transformation into other valuable heterocycles, demonstrating its potential in organic synthesis.
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Rh(III)‐Catalyzed Selective C‐H Alkylation and Alkenylation of 1,2,3‐Benzotriazinones with Maleimides Adv. Synth. Catal. (IF 4.4) Pub Date : 2024-06-25 Shang-Shi Zhang, Lin Xiao, Dan-Ting Shen, Wen-Xuan Zou, Jia-Lin Song, Jiaohang Wei, Xiang Liu, Luyong Zhang
Herein, we describe a condition‐based switchable Rh(III)‐catalyzed C‐H alkylation and alkenylation of 1,2,3‐benzotriazinones with maleimides, where triazinone serves as a directing group rather than its traditional role denitrogenative precursor. This strategy enables the selective synthesis of diverse 3‐arylated succinimides and 3‐arylated maleimides in up to 99% yield with broad substrate scope (48