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Green Synthesis of 3,4-Unsubstituted Isoquinolones through Rhodium(III)-Catalyzed C‒H Activation and Annulation in Ethanol Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-27 Vikash Kumar, Gandeepan Parthasarathy
A mild and convenient synthesis of 3,4-unsubstituted isoquinolones has been achieved from N-methoxybenzamides and vinylene carbonate as an acetylene surrogate with a versatile rhodium(III) catalyst. The reaction proceeded at room temperature in biomass derived ethanol solvent. This protocol avoids the use of stoichiometric external oxidant, as the vinylene carbonate served as the internal oxidant.
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K2S2O8 Mediated C-3 Formylation of Imidazopyridines Using Glyoxylic Acid Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-26 Harish K Indurthi, Samarpita Das, Pallavi Saha, Deepak Sharma
A metal-free formylation of imidazopyridines with K2S2O8 via direct decarboxylative cross-coupling of glyoxylic acid is described. This reaction features broad substrate scope, good functional group tolerance, and generate products in good yields. The involvement of radicals in the course of the reaction has been demonstrated by radical trapping experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl
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DBU Promoted Deformylative/Dehalogenative Difunctionalization to Access β-Bromovinyl Aldehydes Derived from Tetralones** Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-28 Madan Sau, Sapana Dubey, Shreya Roy, Shubhankar Samanta, Tapas Das
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A Dual Photoredox- and Cp2TiCl2-Catalyzed Approach for the Direct Access to α-Vinyl-β-hydroxy Esters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-27 Emanuele Pinosa, Andrea Gualandi, Andrea Fermi, Paola Ceroni, Pier Giorgio Cozzi, Francesco Calogero
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Synthesis of Upper-Rim Sulfanylpropyl- and p-Methoxyphenylazo-Substituted Calix[4]arenes as Chromogenic Sensors for Hg2+ and Ag+ Ions J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Jia-De Lian, Hsin-Yu Hu, Yi-Han Lin, Putikam Raghunath, Ming-Chang Lin, Wen-Sheng Chung
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Computational Exploration of the Thermal Rearrangement of Basketene: One Forbidden versus Two Allowed Pericyclic Reactions J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Xiaolin Yue, Qingyang Zhou, K. N. Houk
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Carboxylate Catalysis: A Catalytic O-Silylative Aldol Reaction of Aldehydes and Ethyl Diazoacetate J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Saara Riuttamäki, Anton Bannykh, Petri M. Pihko
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Dual Palladium-Photoredox-Mediated Regioselective Acylation of Carbazoles and Indolines J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 M. Shahid, A. J. Punnya, Sakamuri Sarath Babu, Subhendu Sarkar, Purushothaman Gopinath
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Adamantylidenecarbene: Photochemical Generation, Trapping, and Theoretical Studies J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Alexander D. Roth, Christine E. Wamsley, Sarah M. Haynes, Dasan M. Thamattoor
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Palladium-Catalyzed Intermolecular Dearomatization Annulation Cascade Reaction of Furans for Stereoselective Access to 2,5-Dihydrofurans J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Lin Lu, Haiyang Huang, Shanshan Yang, Jiang Bai, Yirong Zhou, Qiang Xiao
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Structures and Reactivities of N-Alkenyl-Substituted Anilides: The “Magic” Methyl Effect on Alkene J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Ryu Yamasaki, Mariko Ono, Kento Morita, Ai Ito, Kazuo Fukuda, Iwao Okamoto
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Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Jia-Jia Liao, Ren-Gui Tian, Shi-Kai Tian
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N-Sulfenylation of β-Lactams: Radical Reaction of N-Bromo-azetidinones by TEMPO Catalysis J. Org. Chem. (IF 3.6) Pub Date : 2023-09-28 Valentina Giraldi, Francesco Giunchino, Maria Edith Casacchia, Andrea Cantelli, Marco Lucarini, Daria Giacomini
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Thermodynamic and Kinetic Characteristics of Molnupiravir Tautomers and Its Complexes with RNA Purine Bases as an Explanation of the Possible Mechanism of Action of This Novel Antiviral Medicine: A Quantum-Chemical Study J. Org. Chem. (IF 3.6) Pub Date : 2023-09-27 Wojciech Piotr Oziminski, Agata Bycul
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Mechanism and Origins of Regio- and Stereoselective Alkylboration of Endocyclic Olefins Enabled by Nickel Catalysis J. Org. Chem. (IF 3.6) Pub Date : 2023-09-27 Man Chen, Yi-Wen Gu, Wei Deng, Zheng-Yang Xu
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Organocatalytic Asymmetric [4 + 2] Cyclization of Azadienes with Azlactones: Access to Chiral 3-Amino-δ-Lactams Derivatives J. Org. Chem. (IF 3.6) Pub Date : 2023-09-26 Wu-Jingyun Zhou, Xiaoning Yu, Chen Chen, Wei Lan, Gu Zhan, Jin Zhou, Qian Liu, Wei Huang, Qian-Qian Yang
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Convergent Syntheses of Isomeric Imidazolospiroketones as Templates for Acetyl-CoA Carboxylase (ACC) Inhibitors J. Org. Chem. (IF 3.6) Pub Date : 2023-09-26 Chris Limberakis, Aaron C. Smith, Scott W. Bagley, Hatice G. Yayla, Daniel W. Kung, David A. Griffith
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Late-Stage Diversification of Peptides via Pd-Catalyzed Site-Selective δ-C(sp2)-H Fluorination and Amination J. Org. Chem. (IF 3.6) Pub Date : 2023-09-26 Jian Tang, Fengjie Lu, Yi Sun, Guodong Zhang, Ensheng Zhang, Yuan-Ye Jiang
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Reductive N-Formylation of Nitroarenes Mediated by Rongalite Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Huai-Yu Wang, Xiang-Long Chen, Chun-Yan Wu, Dong-Sheng Yang, Ting Chen, An-Xin Wu
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Rhodium-Catalyzed Hydrolytic Cleavage of the Silicon–Carbon Bond of Silacyclobutanes to Access Silanols Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Wei-Ke Zhu, Hua-Jie Zhu, Xiao-Jun Fang, Fei Ye, Jian Cao, Zheng Xu, Li-Wen Xu
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Stereoselective Synthesis of Indolyl-C-glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2-Alkynylanilines with Glycals Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Xiao Xiao, Puren Han, Jie-Ping Wan, Jianchao Liu
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Modular Synthesis of α-Aryl-α-Heteroaryl α-Amino Acid Derivatives via a Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction Using Air as the Sole Oxidant Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Xiangxiang Kong, Jing Ren, Jinlong Li, Yu Liu, Kaizhi Li
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Boron-Assisted Cobalt-Catalyzed C–H Methylation Using CO2 and H2 Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Qin Shi, Haiyan Hu, Minxing Du, Yajun Sun, Yudong Li, Yuehui Li
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Synthesis of Polysubstituted Furans via Rh(II)-Catalyzed [2 + 3] Annulation of N-Sulfonyl-1,2,3-triazoles with Enaminones Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Xiaoqiang Lei, Juan Feng, Qinglan Guo, Yuanhe Li, Jiangong Shi
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Electrooxidative Fluorofunctionalization of Arylcyclopropanes Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Yanni Yue, Yang Song, Shuaishuai Zhao, Chi Zhang, Chuan Zhu, Chao Feng
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Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Dusty Cadwallader, Dmytro Shevchuk, Tristan R. Tiburcio, Christine M. Le
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Dehalogenative Arylation of Unactivated Alkyl Halides via Electroreduction Org. Lett. (IF 5.2) Pub Date : 2023-09-28 Jinping Lan, Weijie Yu, Ke You, Mengyu Xu, Bin Zhang, Yuanquan Wang, Tao Wang, Jin Luo
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Visible-Light-Enabled Lanthanum-Mediated Intramolecular Epoxy-Ring Opening/Dehydrogenative Lactonization Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Lina Cai, Qihong Lai, Lele Zhang, Guotao Xue, Yirui Zhang, Na He, Mingqiang Huang, Shirong Hu, Shunyou Cai
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Pd-Catalyzed Regioselective Hydroformylation of Olefins with HCO2H and Its Derivatives Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Wenlong Ren, Jinzi Huang, Yian Shi
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Total Synthesis of a Linear Tetrasaccharide Repeating Unit of Vibrio vulnificus MO6-24 Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Antara Ghosh, Suvarn S. Kulkarni
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Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Zhen Li, Xiao-Ming Zhang, Fu-Min Zhang, Yong-Qiang Tu
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Cobalt-Promoted Electroreductive Cross-Coupling of Prop-2-yn-1-yl Acetates with Chloro(vinyl)silanes Org. Lett. (IF 5.2) Pub Date : 2023-09-27 Chong-Hui Xu, Zhi-Qiang Xiong, Jing-Hao Qin, Xin-Hua Xu, Jin-Heng Li
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Site-Selective Nitration of Aryl Germanes at Room Temperature Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Amit Dahiya, Avetik G. Gevondian, Aymane Selmani, Franziska Schoenebeck
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Stereoselective formal alkenylation of β,β-disubstituted enesulfinamides for constructing 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic α-quaternary stereocenters Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-28 Chong-Lin Zhu, Chong-Dao Lu
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Recent Progress on Radiofluorination using Metals: Strategies for Generation of C-18F Bonds Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-27 Truong Giang Luu, Hee-Kwon Kim
C-F bond formation is an important research topic in organic synthesis because of the wide use of organofluorine compounds in various areas including pharmaceuticals, agricultural applications, and materials science. In particular, C-18F bond formation by incorporation of fluorine-18 (18F) with organic molecules is an important process to produce 18F-labeled radiotracers, which are commonly used in
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Regioselective heterofunctionalization of alpha-aryl amides with heteroatom nucleophiles via electrophilic activation Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-27 Shuai Han, Yu Guo, Wei Zhang, Jinjin Chen, Zhen Wang, Yao-Fu Zeng
A general and efficient strategy for the α-heterofunctionalization of aryloxy activated amides with various nucleophiles including amines, alcohols, phenols, carboxylic acids and thiols has been developed. This reaction proceeded under mild reaction conditions with excellent regioselectivity, and TEA was used as the sole additive. The synthetic values were demonstrated by the late-stage modification
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Nickel-catalyzed reductive coupling of nitroarenes and phosphine oxides to access phosphinic amides Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-25 Meixia Liu, Huimin Hu, Runbo Sun, Haoyuan Li, Anjun Ding, Xiaoyong Liu, Zhengjiang Fu, Shengmei Guo, Hu Cai
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Highly diastereo- and enantioselective synthesis of spiro β-lactams via copper-catalyzed Kinugasa/aldol cascade reaction Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-23 Jie Li, Haowen Ma, Xianqiang Zhong, Shanyue Li, Jiehao Zhang, Yunlin Ao, Wei Zhou, Qian Cai
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Reductive thiolation and oxidative dehydroaromatization of cyclohexanones with primary amines and sodium sulfinates to access o-sulfanylanilines Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-22 Hui Wu, Lin Zhao, Wenting Wang, Yining Yu, Ge Wu
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Challenges and Breakthroughs in Z-Enantioselective Olefin Metathesis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-26 Jennifer Morvan, Antonio Del Vecchio, Jakub Talcik, Dylan Bouëtard, Marc Mauduit
Asymmetric Olefin Metathesis (AOM) represents a highly versatile synthetic tool to lead to relevant chiral building blocks with excellent enantiopurity. As the Z-alkene moiety is ubiquitous in a wide range of natural products, the development of catalysts which are able to control both the Z-selectivity and the enantioselectivity of metathesis transformations is in high demands. This review aims to
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One-Pot Synthesis of Fused Tetrahydroquinoline-Iminosugar Derivatives Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-26 Jilai Wu, Song Xie, Xin Xu, Ziyi Zhou, Likai Zhou, Chao Wei, Xiaoliu Li, Chen Wu, Hua Chen
An efficient and simple one-pot synthesis of structurally diverse novel tetrahydroquinolin fused iminosugars was developed through the aza-Diels-Alder mechanism. The adaptability of this method has been demonstrated by a variety of imines and D/L-ribose tosylates, and both electron-donating and withdrawing substituted imines are employed in reaction well. In addition, this reaction is characterized
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Copper-Catalyzed α,β-Regioselective (2+4) Cycloaddition of Propargylic Esters Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-26 Guo-Ke Zhang, Shu-Fang Wu, Chen Zhong, Yu-Qi Liu, Da-Hua Wang, Yu-Chen Zhang, Feng Shi
A copper-catalyzed α,β-regioselective (2+4) cycloaddition of propargylic esters with o-hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series of phosphorus-containing six-membered heterocycles in high yields (up to 99 % yield). This reaction represents the first α,β-regioselective (2+n) cycloaddition of propargylic esters via the intermediates of copper−allenylidenes
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Solvent-free Hydrohalogenation and Deuteriohalogenation by ex situ Generation of HX and DX Gas Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-25 Rik Henri Verschueren, Lauren Voets, Jelena Saliën, Tim Balcaen, Wim Michel De Borggraeve
The hydrohalogenation of olefins is one of the most straightforward methods to access alkyl halides. Despite safety hazards, using pure hydrogen halide gas remains the most atom economic way of performing hydrohalogenation reactions. In this work, we describe the solvent-free hydro- and deuteriohalogenation of olefins using down to near-stoichiometric amounts of hydrogen and deuterium halide gas. Two-chamber
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Asymmetric Synthesis of Pantolactone: Recent Advances Eur. J. Org. Chem. (IF 2.8) Pub Date : 2023-09-25 Zhi-Hong Du, Xiao-Xiong Lv, Ning Liu, Fei Chen, Meng Yuan, Chao-Shan Da
(R)-Pantolactone, an intermediate in the syntheses of Vitamin B5 and coenzyme A, is an important chiral molecule often used as a food additive, chiral auxiliary, and chiral starting material for organic transformations. Enantioenriched pantolactones are predominantly produced by biological fermentation and chemical synthesis approaches. Herein, we present a review of recent developments in the asymmetric
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Core-Labeling (Radio) Synthesis of Phenols Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Colin F. Lynch, Joseph W. Downey, Yongliang Zhang, Jacob M. Hooker, Mark D. Levin
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Fluorine-Activated and -Directed Allene Cycloadditions with Nitrile Oxides and Imine Oxides: Synthesis of Ring-Fluorinated Isoxazole Derivatives Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Kohei Fuchibe, Kazuki Sakon, Kyosuke Suto, Reo Eto, Sho Nakazono, Junji Ichikawa
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Silver(I)-Catalyzed Diastereoselective Hydroborylation of Cyclopropenes J. Org. Chem. (IF 3.6) Pub Date : 2023-09-26 Ming Huang, Changsheng Zhou, Ke-Fang Yang, Ze Li, Guo-Qiao Lai, Pinglu Zhang
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Synthesis of Trifluoromethylated Dibenzoxepines via Palladium-Catalyzed Tandem C–O Bond Formation/C–H Arylation J. Org. Chem. (IF 3.6) Pub Date : 2023-09-25 Zhi-Yi Zhao, Xing-Guo Zhang, Hai-Yong Tu
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Opportunities for Machine Learning and Artificial Intelligence to Advance Synthetic Drug Substance Process Development Org. Process Res. Dev. (IF 3.4) Pub Date : 2023-09-25 Daniel J. Griffin, Connor W. Coley, Scott A. Frank, Joel M. Hawkins, Klavs F. Jensen
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Base-Promoted Tandem Synthesis of 2-Substituted Indoles and N-Fused Polycyclic Indoles Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Fan Zhou, Huimin Jin, Yuanhang Zhang, Jie Li, Patrick J. Walsh, Shengzhang Lin
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Net Intermolecular Silyloxypyrone-Based (5+2) Cycloadditions Utilizing Amides as Enabling and Cleavable Tethers Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Susanna N. Angles, Wentao Guo, Kwabena Darko, Marymoud Erzuah, Kenneth G. Pauley, Ifeanyichukwu E. Promise, John R. Goodell, Dean J. Tantillo, T. Andrew Mitchell
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[Cp*IrCl2]2-Catalyzed Amidocarbonation of Olefins with Sulfoxonium Ylides toward Functionalized Isoindolin-1-ones Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Qi Yang, Junxue Bai, Han Yang, Yang Yao, Yingming Yao, Jianwei Sun, Song Sun
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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Mingshuai Zhang, Longkun Chen, Haifeng Sun, Zhuoyuan Liu, Sheng-Jiao Yan, Fuchao Yu
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Asymmetric Formal Coupling of β-Ketoesters with Quinones Promoted by a Chiral Bifunctional N-Heterocyclic Olefin Org. Lett. (IF 5.2) Pub Date : 2023-09-26 Sijing Wang, Jia Yang, Hongkun Zeng, Yuqiao Zhou, Fei Wang, Xiaoming Feng, Shunxi Dong
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Hard–Soft Cooperativity of an Allosteric Tweezer Org. Lett. (IF 5.2) Pub Date : 2023-09-25 Suk-il Kang, Hyun Lee, Sungryul Bae, Dongwhan Lee
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Synthesis of α-Hydroxyl and α-Amino Pyridinyl Esters via Photoreductive Dual Radical Cross-Coupling Org. Lett. (IF 5.2) Pub Date : 2023-09-25 Xian-Chao Cui, Hu Zhang, Hao Zhang, Yi-Ping Wang, Jian-Ping Qu, Yan-Biao Kang
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Synthesis of Tetrasubstituted 1,4-Dicarbonyl (Z)-2,3-Dihaloalkenes via Electrophilic Halogenation of Alkynyl Hydrazones Org. Lett. (IF 5.2) Pub Date : 2023-09-25 Akashdeep Sharma, Paru Jamwal, Ramani Gurubrahamam
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Palladium catalyzed tandem cyclization of acryloylbenzamides and N-arylacrylamides with epoxides: Access to functionalized isoquinolinediones and oxindoles Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-26 Xiao-Yu Lu, Fu-Yi Shui, Xiang Zhang, Rui Huang, Zi-Zhen Wang, Yi-Wei Song, Fang Jiang, Gui-Xiang Yang, Yan-Xi Sun
Herein, a practical and efficient tandem cyclization ring-opening coupling of acryloylbenzamides and N-arylacrylamide with epoxides was reported. Various acryloylbenzamides and N-arylacrylamide containing a wide range of functional groups coupled with both acyclic and cyclic epoxides to provide the efficient synthesis of valuable hydroxyalkylated isoquinolinediones and oxindoles. These fragments are
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Site-selective C−H difunctionalization of N-alkyl activated azaarenes via the synergistic catalysis of graphene oxide and visible light Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-26 Dehao Duan, Hai-Ping He, Weiyi Ding, Dongcheng Yi, Yingzhen Lai, Aiqiong Huang, Jie Liu, Wengle Wu, Xiangjun Peng
Strategies for site-selective C−H difunctionalization on N-alkyl activated azaarenes have attracted considerable attention as a powerful tool in heterocyclic chemistry. By employing graphene oxide (GO) as heterogeneous cocatalyst, the visible light-induced site-selective difunctionalizations of pyridiniums/quinoliniums provided a distinct and straightforward synthetic route toward C4- and C2-selective
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Why is Phenyl Azide so unreactive in [3+2] Cycloaddition reactions? Demystifying Sustmann’s Paradigmatic Parabola Org. Chem. Front. (IF 5.4) Pub Date : 2023-09-26 Luis R. Domingo, Mar Ríos-Gutiérrez, Patricia Perez
TThe [3+2] cycloaddition (32CA) reactions of phenyl azide with a series of 25 ethylenes of different electronic activation have been studied within Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) computational level to understand the low reactivity of azides participating in 32CA reactions. Analysis of the reactivity indices allows characterizing phenyl azide as a moderate electrophile