Article
Chemistry, Organic
Masayuki Kubo, Naomi Inayama, Eisuke Ota, Junichiro Yamaguchi
Summary: Dance reactions on aromatic rings provide a powerful tool in organic chemistry to move functional groups. By combining with transition-metal-catalyzed coupling reactions, dance reactions of halides and pseudohalides offer a unique platform for the synthesis of diverse substituted aromatic compounds.
Review
Chemistry, Multidisciplinary
Naish Lalloo, Conor E. Brigham, Melanie S. Sanford
Summary: Transition-metal-catalyzed decarbonylative coupling reactions using carboxylic acid derivatives as electrophiles have the advantages of abundant and inexpensive reactants. This Account highlights the development of base-free decarbonylative coupling reactions catalyzed by group 10 metals and discusses the catalyst design guided by stoichiometric organometallic studies. The article also discusses the challenges and future directions in this field.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Yunfei Peng, Ryota Isshiki, Kei Muto, Junichiro Yamaguchi
Summary: Ni or Pd-catalyzed decarbonylative reductive couplings of aromatic esters were developed, which can be applied to a range of aromatic esters for homocoupling reactions, and a nonsymmetrical biaryls system can be obtained through a decarbonylative cross-coupling reaction between two different aromatic esters.
Article
Chemistry, Organic
Xiao-Yu Lu, Meng-Yuan Ge, Ting-Hua Tao, Xiao-Mei Sun, Meng-Ting Gao, Shu-Ting Bao, Qi-Le Liu, Ze-Jie Xia, Jing Xia
Summary: This study presents a novel and practical strategy for constructing monofluoroalkenes from aliphatic aldehydes, which are key functional groups in synthetic transformations in pharmaceutical and agrochemical sciences. The reaction showed excellent Z-stereoselectivity with moderate to high yields using alpha-fluoro cinnamic acids and aliphatic aldehydes as substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Chengwei Liu, Michal Szostak
Summary: Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis involves in situ activation of carboxylic acids to form aryl-Pd intermediate, followed by coupling with alkynes to generate new C(sp(2))-C(sp) bonds efficiently. This methodology can be applied to the derivatization of pharmaceuticals and mechanistic studies suggest the decarbonylation precedes transmetalation in this process.
Article
Chemistry, Applied
Jin-Hua Bai, Xiu-Juan Qi, Wei Sun, Tian-Yang Yu, Peng-Fei Xu
Summary: This report presents a method for Ni-catalyzed intramolecular decarbonylative coupling, allowing the conversion of areneselenol esters to diaryl selenides. The catalyst, which is inexpensive and readily available, can be used under mild reaction conditions to construct structurally diverse diaryl selenides, including heterocyclic and natural product derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Lingyun Yao, Yan Shang, Jian-Shu Wang, Ailin Pan, Jun Ying, Xiao-Feng Wu
Summary: This palladium-catalyzed carbonylative synthesis efficiently converts 2-alkynylanilines and aryl iodides into N-acyl indoles using TFBen as the CO source, resulting in high yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xinyi Li, Long Liu, Tianzeng Huang, Zhi Tang, Chunya Li, Wenhui Li, Tao Zhang, Zhaohui Li, Tieqiao Chen
Summary: A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis without the use of excess oxidants, providing a relatively general method for preparing internal alkynes.
Article
Chemistry, Organic
Han Cao, Xuejing Liu, Fusheng Bie, Yijun Shi, Ying Han, Peng Yan, Michal Szostak, Chengwei Liu
Summary: This study presents a general and practical palladium-catalyzed intramolecular decarbonylative coupling of thioesters with excellent functional group tolerance and broad substrate scope, using commercially available, cheap, and practical Pd(OAc)(2) catalyst and phosphine ligands under base-free conditions. This versatile protocol is easily performed on a gram scale and applied in late-stage drug derivatization.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Alexander Bunnell, Naish Lalloo, Conor Brigham, Melanie S. Sanford
Summary: This report describes a Pd-catalyzed decarbonylative coupling reaction for the synthesis of difluorobenzyl-substituted (hetero)arenes using (hetero)aryl boronate esters. The reaction was found to be highly selective and effective for a range of electronically diverse boronate esters and substituted difluorobenzyl glutarimides.
Article
Multidisciplinary Sciences
Wen Zhang, Lingxiang Lu, Wendy Zhang, Yi Wang, Skyler D. Ware, Jose Mondragon, Jonas Rein, Neil Strotman, Dan Lehnherr, Kimberly A. See, Song Lin
Summary: Recent research in medicinal chemistry has found a correlation between an increase in sp(3) carbons in drug candidates and their improved success rate in clinical trials. This study focuses on the development of robust and selective methods for constructing carbon(sp(3))-carbon(sp(3)) bonds. By using electrochemistry, the researchers achieve the selective activation of alkyl halides based on their electronic and steric properties, allowing for high selectivity in carbon(sp(3))-carbon(sp(3)) cross-electrophile coupling. This new protocol shows improved chemoselectivity and does not require a transition metal catalyst.
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Alejandro Cervantes-Reyes, Aaron C. Smith, Gary M. Chinigo, David C. Blakemore, Michal Szostak
Summary: This study reports a method for the direct synthesis of nitrogen-containing heteroaromatic biaryls by decarbonylative Pd-catalyzed Suzuki cross-coupling. The practical and modular nature of this method enables the synthesis of diverse heterobiaryl products in excellent yields.
Article
Chemistry, Physical
Chao Liu, Liangliang Song, Luc Van Meervelt, Erik V. Van der Eycken
Summary: An excellent chemo- and regioselective palladium-catalyzed cascade intermolecular N-arylation/aryl-aryl coupling process has been developed, resulting in the synthesis of diverse C4-substituted phenanthridinones. The method shows broad substrate scope and excellent functional group tolerance, allowing for further derivatization to prepare multiple-substituted phenanthridinones in moderate to high yields.
MOLECULAR CATALYSIS
(2021)
Editorial Material
Chemistry, Organic
Chengwei Liu, Michal Szostak
Summary: The decarbonylative Sonogashira cross-coupling reaction utilizes carboxylic acids as substrates to produce arylalkynes, offering a novel synthetic avenue.
ORGANIC CHEMISTRY FRONTIERS
(2021)
