Review
Environmental Sciences
Jinlin Deng, Peili Chen, Shengpeng Xia, Min Zheng, Da Song, Yan Lin, Anqi Liu, Xiaobo Wang, Kun Zhao, Anqing Zheng
Summary: This article reviews the mechanism, catalysts, and other key factors for olefin production through methane oxidative coupling (OCM). The commonly used catalysts and the application of chemical looping oxidative coupling of methane (CLOCM) are discussed. These studies provide important guidance and support for understanding and applying the mechanism of olefin production.
Article
Chemistry, Multidisciplinary
Xiangli Yi, Runze Mao, Lara Lavrencic, Xile Hu
Summary: The study presents a decarboxylative coupling reaction using photoredox and copper catalysis to convert alkyl carboxylic acids into polyfluoroaryl compounds. The method demonstrates broad scope and good functional group compatibility, with the potential to achieve a wide range of F-substitution patterns on the aryl groups. Mechanistic study suggests a [Cu-(Ar-F)(2)] species may be responsible for the transfer of polyfluoroaryl groups to alkyl radicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Sangeth Jenthra, Totan Mondal, Gregor Kemper, Marcus Lantzius-Beninga, Markus Hoelscher, Walter Leitner
Summary: A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids and terminal olefins was achieved using a catalytic system composed of Pd(OAc)(2) in the presence of phosphine-sulfonamido ligands. The bulky ligand L1 favored the formation of 1,1-disubstituted branched olefins with high selectivity, while the less bulky ligand L2 resulted in the formation of 1,2-disubstituted linear products in high yield. Detailed mechanistic investigation revealed that the aryl substituent at the sulfonamide group of ligand L1 favored 1,2-insertion, while the less bulky ligand L2 favored 2,1-insertion.
Review
Chemistry, Organic
Wu Yechun, Yu Jintao
Summary: This review focuses on the recent advances in the acylation/cyclization reaction triggered by acyl radicals that formed from the decarboxylation of alpha-keto acids.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ge Wu, Xueying Zhou, Caihong Wang
Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
CHINESE CHEMICAL LETTERS
(2022)
Review
Chemistry, Multidisciplinary
Velayudham Ramadoss, Yue Zheng, Xiaoqing Shao, Lifang Tian, Yahui Wang
Summary: Carboxylic acids are considered environmentally benign alternatives in various organic transformations due to their non-toxic, stable, and inexpensive properties. Electrochemical decarboxylation has emerged as an efficient methodology for carbon-carbon or carbon-heteroatom bond formations, providing a green and sustainable protocol without the need for chemical oxidants and strong bases. This method also shows good tolerance with various functional groups.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Organic
Zhu Yuxi, Xiao Ting, Xia Dong, Yang Wenchao
Summary: Decarboxylation of fluoroalkyl carboxylic acid derivatives is an effective method to obtain fluoroalkyl radicals, which can participate in tandem and addition reactions to synthesize diverse fluorine-containing molecules. This review summarizes the recent research progress in radical reactions induced by decarboxylation of fluoroalkyl carboxylic acids, including reaction design, mechanism, and future perspectives.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Benxiang Zhang, Yang Gao, Yuta Hioki, Martins S. Oderinde, Jennifer X. Qiao, Kevin X. Rodriguez, Hai-Jun Zhang, Yu Kawamata, Phil S. Baran
Summary: “Cross-coupling reactions are powerful tools for rapidly assembling complex molecules, but their use is limited by traditional oxidative electrolytic protocols. This study demonstrates a mildly reductive Ni-electrocatalytic system that enables coupling of different carboxylates through in situ generation of redox-active esters. This simple and versatile method offers a powerful new approach for synthesis by heterocoupling various levels of redox-active esters.”
Article
Chemistry, Organic
Jenna N. Humke, Ryan A. Daley, Aaron S. Morrenzin, Sharon R. Neufeldt, Joseph J. Topczewski
Summary: This study investigates the mechanistic details of the palladium-catalyzed decarboxylative cross-coupling of sodium benzoates and chloroarenes. The reaction was found to be first-order in Pd, with minimal substituent effect observed for chloroarenes. Palladium-mediated decarboxylation was identified as the turnover-limiting step. The addition of exogenous XPhos was shown to significantly increase catalyst turnover number and improve reproducibility.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Grace A. Lutovsky, Samuel N. Gockel, Mark W. Bundesmann, Scott W. Bagley, Tehshik P. Yoon
Summary: In this study, a direct decarboxylative cross-coupling of native carboxylic acids with nucleophilic coupling partners mediated by inexpensive and non-toxic Fe(III) salts was reported. This method involves an initial photochemical decarboxylation followed by radical-polar crossover, enabling the construction of diverse carbon-carbon, carbon-oxygen, and carbon-nitrogen bonds with remarkable generality.
Review
Chemistry, Organic
Wei Chen, Qiang Liu
Summary: The oxidative coupling reaction of enol derivatives provides an efficient method for the direct construction of carbon-carbon bond in synthetic chemistry. Although chemists began to pay more attention to this reaction in the 1970s, it has rapidly developed in recent years in the field of synthetic methodology and total synthesis of natural products.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Benxiang Zhang, Jiayan He, Yang Gao, Laura Levy, Martins S. Oderinde, Maximilian D. Palkowitz, T. G. Murali Dhar, Michael D. Mandler, Michael R. Collins, Daniel C. Schmitt, Philippe N. Bolduc, Teyu Chen, Sebastian Clementson, Nadia Nasser Petersen, Gabriele Laudadio, Cheng Bi, Yu Kawamata, Phil S. Baran
Summary: Modern retrosynthetic analysis in organic chemistry is a method that guides the design of synthetic routes based on the polar relationships between functional groups. This approach assigns charges to functional groups and disconnects bonds between them. It has applications in undergraduate curriculum and synthetic methods, but requires careful considerations to overcome selectivity and oxidation state issues. In this study, a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids was reported, enabling a simplified approach to accessing complex molecular architectures.
Review
Chemistry, Medicinal
Feiyan Zhan, Jingjie Zhu, Shaowen Xie, Jinyi Xu, Shengtao Xu
Summary: Bioorthogonal coupling reactions have gained significant interest for their substrate selectivity and less restrictive reaction conditions, making them powerful tools in drug development. This review discusses the current applications of bioorthogonal coupling reactions in compound library building, druggability optimization, and intracellular self-assembly platforms, presenting a new trend in drug development for accelerating lead compound screening and expanding the variety of designed compounds.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Applied
Ye Tian, Meibo Duan, Jialu Liu, Siyu Fu, Kuan Dong, Hao Yue, Yunlei Hou, Yanfang Zhao
Summary: Vinyl benzoxazinanones, serving as versatile building blocks, can undergo transition-metal-catalyzed decarboxylation to enable various interesting transformations and annulations.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Hu Jiayu, Zhu Zhiqiang, Xie Zongbo, Le Zhanggao
Summary: This review highlights the recent progress in photocatalytic decarboxylative coupling reactions of alpha-amino acid derivatives. Amino acids are important biomass raw materials that can be used for the synthesis of various organic compounds, showing high synthesis efficiency and sustainability.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
