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Gold-Zinc Co-Catalyzed Alkynoate Hydrocarboxylation with N-Protected Amino Acids for Preparation of Storable Acylating Reagents and Racemization-Free Peptide Synthesis Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-18 Ayaka Sakurada, Miyu Sato, Kosuke Higashida, Masaya Sawamura
Hydrocarboxylation of methyl 2-octynoate, a chemical commercially available at a low cost, with N-protected amino acids was developed with a gold-zinc cooperative catalyst constructed with a 5-[(2,2'-bipyridin)-5-yl]imidazo[1,5-a]pyridin-3-ylidene to prepare α-methoxycarbonyl enol esters as acylating reagents. The α-methoxycarbonyl enol esters were isolable through silica-gel column chromatography
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Visible Light‐Enabled Decarboxylative Alkylation of Quinoxalin‐2(1H)‐ones using Alkyl Carboxylic Acids via Energy Transfer Process Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-20 Anoop Sharma, Nihal Singh, Raman Kumar, Anuj Sharma
Here in, we describe the photochemical decarboxylative alkylation of quinoxalin‐2(1H)‐ones using commercially accessible carboxylic acids with oxygen as sole oxidant through energy transfer process. The coupling of diverse array of alkyl carboxylic acids (1o to 3o) and bioactive acids with quinoxalin‐2(1H)‐ones is successfully accomplished to achieve the desired alkylated products.
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Visible‐light mediated Ugi‐type reaction for the synthesis of 3,3‐disubstituted phthalides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-20 Feiyu Gao, Chenxin Yin, Yi He, Shuang Zhao, Mengxiao Chen, Jia Zheng, Dan Ni, Houhua Yin, Xian Fu, Xiaoyong Zhang, Shenyou Nie
The synthesis of diverse phthalides containing quaternary carbon centers remains poorly exploited, requiring stepwise reactions with toxic reagents under high temperatures. Herein, we describe a visible‐light promoted, photo‐ and metal‐catalyst‐free protocol for the modular synthesis of 3,3‐disubstituted phthalides with water as the sole by‐product. This process featured an open‐flask operation of
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Improved Palladium Catalysis in Suzuki‐Type Coupling of Benzotriazinones for o‐Aryl/Alkenyl Benzamides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-20 Minling Xü, Ke Xü, Gang Zou
A palladium catalyst system based on PdCl2(PPh3)2 or PdCl2(dppf) is reported for Suzuki‐type coupling of both N‐aryl and alkyl benzotriazinones with aryl/alkenyl boronic acids to afford a series of ortho‐aryl/alkenyl benzamides in yields up to 99%, showing improvements on catalytic efficiency, substrate scope and practicality. Scope and limitations of the improved protocol have been demonstrated with
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A Mild Metal‐Free Approach for the Direct Synthesis of Carbamoyl Azides from Carboxylic Acid Redox Active Esters Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-20 Yan-Hua Qiu, Yuping Zhu, Ming-Hua Rao, Chang-Qi Huang, Zi-Ying Huang, Zhengwang Chen, Jinbin Zhu, Daohong Yu
Carbamoyl azide is an important compound which was transformed into urea, amine and applied to nitrene insertion reaction. We developed a novel metal‐ and oxidant‐free method for the direct synthesis of carbamoyl azide from acid redox active esters. A variety of functional groups were tolerated. In addition, the late‐stage modification of natural products and drugs paves the way for the design and
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Copper‐catalyzed Alkenylation and Alkenyloxylation with‐Alkenyl(phenyl)iodonium Salts Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-20 Zhao-Xin Song, Meng-Wei Yang, Teng-Teng Wu, Yun-He Xu
An efficient and straightforward Cu‐catalyzed vinylation method for alkenyl ethers has been developed. This method demonstrates outstanding performance, delivering high yields and remarkable stereoselectivities for both cyclic and chain alkenyl ether substrates. Furthermore, we have successfully applied this method to directly vinylate the C‐2 position of protected glucals, offering a valuable tool
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Synthesis of 2‐Amino‐3‐arylindoles and their Fused Analogues via Intramolecular C‐Arylation. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 K. Žáková, P. Králová, M. Soural
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Access to Benzyl Oxindoles via Electron Donor–Acceptor Complex Photoactivation Using Thianthrenium Salts and Potassium Carbonate Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 Pau Sarró, Albert Gallego Gamo, Roser Pleixats, Adelina Vallribera, Carolina Gimbert Suriñach, Albert Granados Toda
A photochemical synthesis of biologically relevant benzyl oxindoles is presented via electron‐donor acceptor (EDA) complex strategy. This exogenous photocatalyst‐free method describes the formation of a new electron donor‐acceptor complex based on potassium carbonate and thianthrenium salts for C(sp2)–C(sp3) bond formation. This transition‐metal free reaction allows a rapid increase in oxindoles molecular
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Gold‐Catalyzed Synthesis of Ortho‐Quinone Methide Analogues as Reactive Synthetic Precursors. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-19 T. Yamada, A. Fujii, C. Furugen, K. Kobayashi, T. Hyodo, T. Ikawa, H. Sajiki
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Palladium‐Catalyzed Two‐fold Annulation Reaction of 2,6‐Dihalogenobiphenyls with o‐Chloroaromatic Carboxylic Acids to Access (Aza)dibenzo[fg,op]tetracenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-18 Ji-Fa Zhu, Song Li, Xin-Yuan Long, Yingbo Shi, Bi-Qin Wang, Chun Feng, Hai-Liang Ni, Shi-Kai Xiang
A palladium‐catalyzed two‐fold annulation reaction of 2,6‐dihalogenobiphenyls with o‐chloroaromatic carboxylic acids has been developed. This method enables the synthesis of various dibenzo[fg,op]tetracenes and azadibenzo[fg,op]tetracenes. Preliminary investigations indicate that the resulting product, dimethyl 5,6,12,13‐tetrakis(hexyloxy)dibenzo[fg,op]tetracene‐2,9‐dicarboxylate, demonstrates favorable
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Acid‐Mediated Condensation of 2‐Aminoaryl Cyclopropyl Ketones with Aldehydes for the Synthesis of 2,3‐Dihydrofuro[3,2‐c]quinolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-18 Wenbo Cai, Cong Zhang, Xin Wang, Chuanjun Song
A method for the synthesis of 2,3‐dihydrofuro[3,2‐c]quinolines via TfOH or TMSOTf mediated condensation of 2‐aminoaryl cyclopropyl ketones with aldehydes has been developed. The reaction proceeds under transition metal or halogen free conditions, giving access to the target molecules in 27‐90% isolated yields. Mechanistic study indicates that the reaction sequence involves imine formation, intramolecular
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Iridium‐Catalysed C(sp3)−H Activation and Hydrogen Isotope Exchange via Nitrogen‐Based Carbonyl Directing Groups Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-18 Nathan Knight, James Thompson, John Andrew Parkinson, David Lindsay, Tell Tuttle, William Kerr
. Growing interest in improved structural diversity within the pharmaceutical industry has led to a focus on more sp3‐rich drug frameworks. Meanwhile, spiralling pharmaceutical research and development costs continue to require expedited adsorption, distribution, metabolism, excretion, and toxicity studies, which are heavily reliant on the use of molecules incorporating deuterium and tritium. Herein
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Stereoselective access to β‐gem‐difluorinated alcohols through enzymatic reduction Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Lucas Bacheley, Julien Boutet, Gérard Guillamot, Pierre Gilles, Juliette Martin, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
We report here a mild and efficient process to access diversely functionalized enantioenriched b‐gemdifluorinated (S)‐alcohols by using biocatalytic reduction in > 99% yield and enantiomeric excesses ranging from 96% to >99%. This novel approach involves enzymatic reduction of α‐gem‐difluorinated heterocyclic and carbocyclic ketone derivatives as well as an acyclic gem‐difluorinated β‐ketosulfone and
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Manganese‐Mediated Electrooxidative Ring‐Opening Azidation of Cyclobutanol Derivatives with TMSN3 Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-17 Wenchao Gao, Jie Yang, Yong Teng, Wendian Li, Wenguang Li, Ting Li
A Mn‐electrocatalytic ring‐opening azidation of tert‐cyclobutanols has been developed. The regioselective method is applicable for the azidation of a diverse array of cyclobutanols to provide γ‐azido ketones in 23‐91% yields under chemical oxidants‐free reaction conditions. Detailed mechanistic studies suggest the process of Mn‐mediated alkoxy radical generation followed by β‐scission to form carbon‐centered
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Cobalt Catalyzed Annulation of Benzimidates or NH‐Benzaldimines with Ynamides : Synthesis of 1‐Alkoxy‐ and 1‐Alkyl‐3‐Aminoisoquinolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-13 Isabelle Gillaizeau, Cyril NICOLAS, Elsa Anselmi, pascal retailleau, Liliane Mimoun, Hamdi Sanaa
Inexpensive cobalt‐catalyzed, pivalic acid‐assisted oxidative C‐H functionalization of benzimidates or NH‐benzaldimines with ynamides is presented, providing an access to 3‐aminoisoquinoline derivatives. The procedure is compatible with various substrates featuring alkyl, alkoxy, acyl or halogen as substituents, heteroaryl structures, and diverse ynamides. The reaction has been scaled up, with subsequent
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Organocatalyzed, Three‐Component Construction of Cyanopyrazoles Using Diazoacetonitrile Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-13 Anamika Dhami, Anuj Kumar, Kalathingal Hisana, KISHOR MOHANAN
An organocatalyzed three‐component protocol using diazoacetonitrile to access a wide range of cyanopyrazole derivatives has been reported herein. This strategy, which proceeds through a piperidine‐catalyzed Knoevenagel condensation/formal [3+2] cycloaddition/dehydrocyanation sequence, provides an efficient route to construct dicyanopyrazoles from aldehydes, malononitrile, and diazoacetonitrile regioselectively
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Copper‐Catalyzed α‐Indolmethylation of 2‐Pyridylacetates with 3‐Indoleacetic Acids via Alkylideneindolenine Intermediates Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-13 Xiaodong Tang, Chen Chen, Yongjun Chen, Jianxin Pang, Weiya Kong
This study reports the copper‐catalyzed α‐indolmethylation of 2‐pyridylacetates with 3‐indoleacetic acids. This reaction offers a approach to generating alkylideneindolenine electrophiles via the oxidative decarboxylation of 3‐indoleacetic acids. The developed reaction system demonstrates good versatility, extending beyond the indolmethylation of 2‐ pyridylacetates to include activated esters and nitroalkanes
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Synthesis of Alkynylsilanes: A Review of the State of the Art Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-12 Krzysztof Kuciński
This contribution offers a comprehensive overview of methods for forging sp C–Si bonds. Over time, alkynylsilanes (silylacetylenes), once considered mere byproducts of hydrosilylation processes, have become essential building blocks in organic synthesis. This literature review traces the evolution of their synthesis, from traditional methodologies relying on organolithium and organomagnesium compounds
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Enantioselective Si‐H Insertion of Arylvinyldiazoesters Promoted by Rhodium(I)/Diene Complexes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-12 Ziyan Li, Jian-Guo Liu, Wen-Ping Zhang, Ming-Hua Xu
An enantioselective Si‐H insertion between α‐arylvinyldiazoesters and silanes has been developed by employing rhodium(I)/chiral diene complex as the catalyst. This protocol offers a catalytic asymmetric approach to various chiral silanes containing α‐arylvinyl functionality at room temperature with good enantiocontrol (89‐99% ee). Transformation of the resulting enantiomerically enriched α‐arylvinyl‐α‐silyl
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Complexes of Borane and 1,3,5‐Triazinane‐Derived Carbenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-11 Vladimir Smirnov, Vitalij Levin, Alexander D. Dilman
Complexes of borane with six‐membered N‐heterocyclic carbenes derived from readily accessible 1,3,5‐triazinium salts are described. Similar to the widely used imidazolium‐type borane complex, the obtained complexes behave as agents for the hydrogen atom transfer in the Giese reaction and as sources of the boryl radicals in addition to imines. The amine nitrogen of these complexes does not undergo alkylation
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Palladium‐Catalyzed/Mn(OAc)3‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N‐Allyl Sulfonamides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-11 Camilla Loro, Marta Papis, Sara Colombo, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Julie Oble
Palladium‐catalyzed conditions for diazidation or acetoxy/hydroxylation of N‐allyl sulfonamides by using Pd(OAc)2 as the catalyst combined with Mn(OAc)3·2H2O have been developed. The 1,2‐diazidation reaction of the carbon‐carbon double bond occurs in mild conditions (i.e. NaN3 as azide source in THF at room temperature), whereas the 1,2‐acetoxy/hydroxylation requires an excess of Mn(OAc)3·2H2O. The
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Solid‐phase Synthesis of Peptidols via Reductive Cleavage through a Benzotriazole Linker Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Szu-Hsuan Chen, Hui-Ying Chuang, Chitra Rajavel, Yi Kai Lin, Shu-Han Chang, Pei-Chen Tsai, Hui-Ting Chen, Chung-Ming SUN, Anand Selvaraj, Chai-Lin kao
Peptidols were prepared through the reductive cleavage of benzotriazole intermediates obtained from the on‐bead activation of 3,4‐diaminobenzoyl linkers. Remarkably, this method used commercially available amino acid residues and resins without further modification. Pure peptidols were collected with only filtration in 49%–87% yield. Only the derivatives with aspartic acid as the first C‐terminal residue
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TBHP‐Mediated Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Iodides to Construct β‐Perfluoroalkyl Alcohols Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Jiantao Zhang, Weiming Zhu, Renhua Su, Duoduo Xiao, Peng Zhou, Kai Chen, Min Zhang, cui chen, Weibing Liu
A three‐component strategy for the synthesis of β‐perfluoroalkyl allyl alcohols from 1,3‐dienes is developed. A diverse range of synthetically valuable β‐perfluoroalkyl allyl alcohols are obtained in moderate to high yields. Broad substrate scope and good functional group tolerance are observed. This method is also applicable to mono‐olefins and 1,3‐enynes. The control experiment results demonstrate
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n‐Bu4NI/K2S2O8 Mediated Csp2‐Csp2 Bond Cleavage – Transformylation from p‐Anisaldehyde to Primary Amides Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Xiaochen Liu, Samual Hee, Netanel Sapir, Alvin Li, Jianbo Liu, Yu Chen
n‐Bu4NI/K2S2O8 mediated transformylation from p‐anisaldehyde to primary amides is reported. The mechanistic studies suggest the reaction occurs via a single electron transfer pathway. Based on the DFT electronic structure calculations of various reaction pathways, the most plausible mechanism involves the formation of a phenyl radical cation and an arenium ion as the key intermediates. It represents
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Photocatalyzed formation of gem‐difluoroalkenes using oxime esters Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Lilian Geniller, Marc Taillefer, Eric Clot, Florian Jaroschik, Alexis Prieto
In this manuscript a general photocatalytic approach for the synthesis of alkyl‐substituted gem‐difluoroalkenes using readily‐available oxime esters and 1‐bromo‐1,1‐difluoroprop‐2‐ene (BDFP) has been established. This strategy involving a radical bromo‐elimination provides access to a large variety of value added fluorinated molecules. The mild reaction conditions are compatible with many functional
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Base‐promoted selective synthesis of alkynyl sulfides via C−S bond cleavage of alkynyl sulfonium salts Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-10 Jian Wen, Ziyu Wang, Mengke Su, Hanmiao Xu, Junqi Zhou
An effective one‐pot approach has been devised for the selective synthesis of alkynyl sulfides through the cleavage of C−S bonds in alkynyl sulfonium salts. This method involves a base‐promoted nucleophilic ring‐opening and desulfurization pathway, enabling the efficient preparation of diverse alkynyl sulfide compounds. The reaction demonstrates excellent tolerance to various functional groups and
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Chiral P,N,N‐Ligands for Asymmetric Hydrogenation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-09 Ding-Hua Liang, Chuan-Jin Hou, Qi Li, Hao Qin, Ling Li, Xiang-Ping Hu
The chiral P,N,N‐ligands represented a new type of tridentate ligand developed in recent years and displayed wide utilities in asymmetric catalysis. In the past decades, numerous chiral P,N,N‐ligands with ferrocene, phenethylamine and spiro backbones were synthesized by addition of an aminopyridine, imidazole or diamines coordinating group. These chiral tridentate P,N,N‐ligands showed excellent performance
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Rh(II)‐Catalyzed Homocoupling/[4+1] Cycloaddition Cascade of Diazobarbiturates with Diazopyrazolones to Prepare Spirobarbiturates Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-09 Kuo Wang, Yue Zhang, Yu-Hang Mi, Hong-Wu Zhao, Xiu-Qing Song, Jin-Tao Li, Fang Zhang
Under the catalysis of Rh2(OAc)4 (10 mol%) and (±)‐Me‐Pybox (20 mol%) in 1,2‐DCE at 80℃, the homocoupling/[4+1] cycloaddition cascade of diazobarbiturates with diazopyrazolones proceeded readily and provided spirobarbiturates in 32%–88% chemical yields. The chemical structure of the obtained spirobarbiturates was identified by X‐ray diffraction analysis.
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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-05 Kaixing Gong, Yingchun Ma, Ping Yu, Shulin Gao, Yanni Li, Deqiang Liang, Shaoguang Sun, Baoling Wang
While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well as one with a low photocatalyst loading is presented. These external‐oxidant‐free cyclizations are enabling and applicable to a range of activated alkenes, affording a diverse array of
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Site‐Selective S‐Arylation of 1‐Thiosugars with Aryl Thianthrenium Salts through Copper(I)‐Mediated, Photoredox‐Catalyzed Reactions Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-05 Yi-Ni Fang, Qing Liang, Lingling Shi, Jiayang Wen, Xinzhang Liu, Xuerui Hong, Xiaoming Zha, Fei Ji
A process for the synthesis of aryl thioglycosides from the aryl thianthrenium salts and 1‐thiosugars is achieved by copper(I)‐mediated, photoredox‐catalyzed reactions. The desired products could be obtained in 32% to 78% yield after irradiation with 34 W blue light at room temperature. Various functional groups, especially including halogen groups, were well tolerated under standard reaction conditions
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Access to 4‐Membered Heterocycles via Visible‐Light Triggered Intramolecular Cyclization from Alkynes: Bypassing Unfavorable 4‐endo‐dig Cyclization Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-05 Arun Sharma, Ahhyeon Choi, Daniel Yim, Hyungjun Kim, Hyunwoo Kim
We describe a catalyst, oxidant, and coupling‐reagent free strategy to access 4‐membered heterocycle, representing a unique example of visible‐light triggered intramolecular cyclization of propargylic alcohols and amines to access oxetanones and azetidinones respectively. Despite the direct 4‐endo‐dig cyclization from these starting materials has proven to be unfavorable, the formation of key p‐quinone
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Phosphine‐Catalyzed Domino Annulation Reactions of o‐Aminotrifluoroacetophenone Derivatives with Morita−Baylis−Hillman Carbonates: Construction of Tetrahydrofuro[3,2‐b]indolines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-05 Yannan Zhu, He Zhao, Qiuyun Li, Bo Fang, Yining Wang, Gang Qi
The domino annulation reactions of o‐aminotrifluoroacetophenone derivatives and MBH carbonates enabled by PPh3 have been reported, which provide a series of tetrahydrofuro[3,2‐b]indolines containing a CF3‐substituted tetrasubstituted carbon stereocenters in yields of 74 to 95% and >20:1 dr. In this process, MBH carbonates were used as C1/C3 synthons. The MTT assay shows that the products exhibit the
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Organoselenium Catalyzed Electrochemical Cascade Cyclization: An Access to Naphthofuran‐2‐carboxaldehyde Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-05 NEHA DAGAR, SWATI SINGH, Sudipta Raha Roy
We have developed an approach for the construction of naphthofuran‐2‐carboxaldehyde derivatives by utilizing the synergy of electrochemical oxidation and organo‐selenium catalysis at room temperature. The compatibility of various functional groups and scalability of this protocol demonstrate the practicality of the electrochemical strategy. The synthetic utility of this strategy is furthermore demonstrated
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N‐Heterocyclic Olefin‐Phosphines Based Cationic Ruthenium Complexes as Pre‐Catalysts for Dual C‐H Bond Functionalizations Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-04 Amiya Kumar Sahoo, Bhagyashree Das, Subhra Jyoti Panda, Chandra Shekhar Purohit, Adinarayana Doddi
Two N‐heterocyclic olefin‐phosphines and the corresponding ruthenium complexes were synthesized and structurally characterized. One of the cationic complexes [(BzIM)(NHOP)Ru(p‐cymene)Cl2]I was employed as a catalyst in N‐benzylbenzamides/alkyne coupling reactions. With this catalytic protocol a variety of substituted isoquinolones were synthesized through ortho‐selective double C‐H bond functionalization
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Insights into the Enantioselective Au(I)‐Catalyzed Reactions between 2‐Alkynyl Ketones and Naphthols using the TCDC approach Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-04 Yunliang Yu, Meriem Daghmoum, Nazarii Sabat, Zhenhao Zhang, gilles frison, Angela Marinetti, Xavier Guinchard
The CPAPhosAuCl bifunctional complexes catalyse the enantioselective tandem cycloisomerization‐nucleophilic addition reactions between 2‐alkynylenones and naphthols, where naphthols behave mainly as O‐nucleophiles. The inherent acidity of the catalysts induces then the isomerization of the O‐addition‐ into the C‐addition products with concomitant decrease of their enantiomeric excesses. In depth mechanistic
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Recent Advances in Radical Transformations of Propargylic Alcohols Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-04 Meng Liang, Haojie Ma, Xian-Rong Song, qiang xiao
Propargylic alcohols are regarded as a class of readily available and versatile synthons in organic synthesis. Due to their unique bifunctional character, the transformation of propargylic alcohols has been widely utilized as a powerful strategy for the construction of various functionalized frameworks over the past few decades. Recently, the radical transformation of propargylic alcohols has attracted
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N‐Tosylhydrazones as [N,N] Synthons in Heterocyclic Chemistry: Synthesis of 3,5‐Disubstituted N‐Alkenyl‐1H‐pyrazoles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-04 Antonio Velázquez-Stavínov, Helena F. Piedra, Aarón Gutiérrez-Collar, Manuel Álvarez-Márquez, M. Isabel Menéndez, Isabel Merino, María-Paz Cabal, Enrique Aguilar
A new mode of reactivity of N‐sulfonylhydrazones towards alkynes is described: ketone‐derived N‐tosylhydrazones (NTHs) bearing α‐H atoms behave as [NN] synthons in their reactions with alkoxy alkynyl Fischer carbene complexes (FCCs) and only the two N atoms are incorporated into the newly formed pyrazole ring. The scope of the reaction, leading to 5‐methoxy‐N‐alkenyl pyrazoles, proved to be wide regarding
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Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-04 Debashis Ghosh, Ancy Sherin, Sumit Ghosh, Sushma A Kalose, Alakananda Hajra
This review presents an outline of current advancements in the photochemical and electrochemical synthesis of oxazoles and isoxazoles. Oxazole and isoxazole are important building blocks for a variety of medicinally useful compounds. Therefore, the synthesis of these heterocycles via sustainable technologies is worth demanding. Photochemical and electrochemical are two among the few sustainable technologies
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3‐Amido‐benzo[b]silines: straightforward modular 2‐step synthesis and photophysical properties Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-04-03 Stéphane Golling, Tiahong Yan, Valérie Mazan, Frédéric R. Leroux, Ilaria Ciofini, Morgan Donnard
In this manuscript we report the synthesis of 3‐amido‐benzo[b]silines thanks to a 2‐step strategy involving a 3‐component silylformylation of ynamides followed by a Friedel‐Crafts cyclization/ isomerizing dehydration domino sequence. This reaction is tolerant to various structural variations and has allowed us to synthesize a library of diversely substituted silacycles with yields from 28 to 85%. We
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Visible Light‐Mediated Defluorination to Access 1,1‐Difluoro‐1,3‐Enynes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-29 Xu Wang, Wei Huang, Feng-Hua Zhang
Herein, a visible light‐mediated defluorination reaction to access 1,1‐difluoro‐1,3‐enynes is described. Compared with previous studies, this protocol employs more readily accessible acids as a radical precursor under the redox‐neutral conditions. Moreover, the reaction exhibits high compatibility with diverse primary, secondary and tertiary acids, especially natural amino acids and drug‐derived acids
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Biocatalytic Regio‐ and Enantiocomplementary Synthesis of Chiral Aryloxazolidinones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-28 Xiaoying Zhou, Yuan-Fei Wang, Hong-Kang Fu, Hui-Hui Wang, Yongzheng Chen, Nanwei Wan
We described the protein engineering of the halohydrin dehalogenase HheG to enhance its R enantioselectivity for the synthesis of chiral 4‐aryloxazolidinones via α‐regioselective ring‐opening of aryl epoxides with cyanate. Additionally, we achieved the inversion of its regioselectivity and enantioselectivity, resulting in a HheG variant tailored for the synthesis of chiral 5‐aryloxazolidinones via
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Synthesizing Silyl Arylsulfonyl hydrazones as Silyldiazomethane Precursors and Their Use in Rhodium‐catalyzed Reactions Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-28 Shuji Tsuruda, Keigo Saito, Tsuyoshi Matsuzaki, Da-Yang Zhou, Takeyuki Suzuki, Makoto SAKO, Mitsuhiro Arisawa, Kenichi Murai
A method for synthesizing silyl arylsulfonyl hydrazones as silyldiazomethane precursors has been developed. Although silyldiazomethanes are an important class of diazo compounds, their use in intramolecular cyclization reactions has not been fully explored despite the rich chemistry of diazo compounds, particularly metal carbenoid chemistry. The fundamental challenge underlying the absence of such
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Diastereoselective Synthesis of High Functionalized 4-Imidazolidinone-Tetrahydro-β-Carboline Hybrids via Divergent Post-Ugi Transformation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-27 Valerio Morlacci, Antonio Arcadi, Massimiliano Aschi, Marco Chiarini, Nicola Demitri, Doriano Lamba, Caterina Momoli, Laura Palombi, Vito Vece
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One-Pot Rh(III)-Catalyzed Twofold C−H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-27 Sergio Otero-Riesgo, Jesús A. Varela, Carlos Saá
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Synthesis of 4,6‐Difluoro‐Tryptophan as a Probe for Protein 19F NMR Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-26 Christina M Monnie, Iker Hernández, Raixie Meléndez-Pacheco, Fatema Bhinderwala, Vadim Soloshonok, Angela M. Gronenborn, Aitor Landa, Mikel Oiarbide
A scalable procedure for the synthesis of 4,6‐difluorotryptophan is reported based on a deaminative coupling of a 4,6‐difluorogramine with 2‐benzylthio‐1,5‐dihydro‐4H‐imidazolone as glycine equivalent. Thus prepared 4,6‐difluorotryptophan was incorporated into the C‐terminal domain of the HIV‐1 capsid protein (CA‐CTD), and 19F spectra of the 4,6‐difluoro Trp CA CTD were recorded and compared to the
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Copper‐Catalyzed Cyanoalkylation and Trifluoromethylthiolation of Styrene Derivatives via a Visible‐Light‐Promoted Cross‐Coupling Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-26 xiao-jing xu, Zhuo-Min Chi, Rong Rui, Zhe Zhang, Hong-Zhe Li, Xue-yuan Liu
Transition‐metal catalyzed difunctionalization of olefins has attracted considerable attention as a method to construct carbon‐carbon and carbon‐hetero bonds. Herein, the copper‐catalyzed three‐component radical cross‐coupling of oxime esters, styrenes, and AgSCF3 through a visible‐light‐promoted iminyl radical‐mediated carbon‐carbon bond cleavage strategy has been described. Utilizing low‐cost copper
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Cationic [1,5]-Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E- and Z-Tetrasubstituted Olefins Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-22 Santu Sadhukhan, Sindoori R. Nair, Beeraiah Baire
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Divergent Synthesis of Di- and Mono-Alkylated Indoles via Tunable Iron-Catalyzed Hydroarylation of Styrenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-22 Le-Wei Miao, Peng Chen, Meng-Xue Hu, Jin Yin, Hongying Du, Yi-Jun Jiang
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I2‐Promoted sp3 C–H Oxidation/Annulation Sequences for the Synthesis of Indoloquinolines from 2‐(1H‐indol‐2‐yl)anilines and Aryl Methyl Ketones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-22 Mariyaraj Arockiaraj, Venkatachalam Rajeshkumar
An iodine/DMSO‐promoted metal‐free approach has been developed for the synthesis of indoloquinolines via a sequential sp3 C‐H oxidation/intramolecular cyclization using 2‐(1H‐indol‐2‐yl)anilines and aryl methyl ketones. A wide range of aryl methyl ketones, including drugs and complex bioactive molecule‐derived substrates were compatible in the present reaction with yields in the range of 30‐96%. This
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Palladium‐Catalyzed Chemoselective Amination of Chloro(hetero)aryl Triflates Enabled by Alkyl‐Pyrazole‐Based Phosphine Ligands. Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-22 C. Gu, O. Y. Yuen, S. S. Ng, C. M. So
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Mechanochemical Mitsunobu Reactions Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-21 Matthew T. J. Williams, Laura Adarve Cardona, Carsten Bolm
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Air-Stable Bis-Cyclometallated Iridium Catalysts for Ortho-Directed C(sp2)−H Borylation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-21 Janis M. Zakis, Antonis M. Messinis, Lutz Ackermann, Tomas Smejkal, Joanna Wencel-Delord
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An iron‐catalyzed three‐component radical cascade cyclization to access cyanoalkylsulfonyl quinolino‐quinazolinones Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-21 Abuthayir Mohamathu Ghouse, Uppalam Tarun, Bathula Maheswari, Srirama Murthy Akondi
An iron(II)‐catalyzed cascade reaction, involving cyanoalkylsulfonylation and cyclization, has been devised to enable the synthesis of functionalized sulfonylated quinolino‐quinazolinone alkyl nitriles. This three‐component radical transformation exhibits excellent chemo‐ and regioselectivity while functioning without the need for external oxidizing or reducing agents. The cost‐effectiveness of this
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Copper‐Catalyzed Aerobic Benzylic C(sp3)−H Oxidation of Unprotected Aniline Derivatives for the Synthesis of Phenanthridines Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-20 Kanako Nozawa-Kumada, Yuta Matsuzawa, Masahito Hayashi, Takumi Kobayashi, Masanori Shigeno, Akira Yada, Yoshinori Kondo
Herein, we report a copper‐catalyzed intramolecular benzylic C(sp3)−H oxidation of unprotected aniline derivatives under aerobic conditions, which enables the preparation of phenanthridine compounds. To the best of our knowledge, this is the pioneering reaction of dehydrogenative C(sp3)−N bond formation from unprotected anilines under a Cu/O2 system. Notably, various anilines possessing alkyl, methoxy
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Direct Catalytic Stereoselective Synthesis of C4′ Functionalized Furanoside and Nucleoside Derivatives with a Tetrasubstituted Stereocenter Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-19 Kaiheng Zhang, Haibo Wu, A. Ken Inge, Armando Córdova
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Chemoselective Oxypalladation of (o-Alkynylaryl)amide-Triggered Site-Selective C−H Annulation for Stereoselective Synthesis of Succinimide-Fused Polycycles Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-19 Dattatri, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
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Access to 3-Azetidines via Halogenation of Titanacyclobutanes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-19 Tyler D. Weinhold, James A. Law, James H. Frederich
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Copper-Mediated Decarboxylative Amidination: Synthesis of O-Methyl-N-Alkylnitroisoureas Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-19 Jonathan Lusseau, Dickson Uduagwu, Frédéric Robert, Yannick Landais
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Electrochemical Oxidative Ring-Opening Reactions of 2H-Indazoles with Alcohols to Obtain Ortho-alkoxycarbonylated Azobenzenes Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-17 Yibin Hu, Xin Liu, Chenglong Feng, Jiaxu Wang, Meichao Li, Zhenlu Shen
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Synthesis of 2-amino-3-arylindoles and their Fused Analogues via Intramolecular C-Arylation Adv. Synth. Catal. (IF 5.4) Pub Date : 2024-03-17 Kateřina Žáková, Petra Králová, Miroslav Soural