Palladium-Catalyzed Thiocarbonylative Synthesis of α,β-Unsaturated Thioesters Using S-Aryl Thioformates as the Thioester Sources

被引:7
|
作者
Shen, Zekai [1 ]
Huo, Yong-Wang [1 ]
Qi, Xinxin [1 ]
Wu, Xiao-Feng [2 ,3 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Key Lab Surface & Interface Sci Polymer Mat Zhejia, Hangzhou 310018, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Liaoning, Peoples R China
[3] Leibniz Inst Katalyse EV, D-18059 Rostock, Germany
关键词
CARBON-MONOXIDE; ASYMMETRIC-SYNTHESIS; THIOL ESTERS; ACETYLENES; BOND; THIOFORMYLATION; DERIVATIVES; COMPLEXES; ALDEHYDES; EFFICIENT;
D O I
10.1021/acs.orglett.3c01400
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed thiocarbonylation reaction forthe synthesis of alpha,beta-unsaturated thioesters from vinyltriflates with S-aryl thioformates as the thioestersources has been developed. The reaction proceeded smoothly at lowtemperature, and a variety of alpha,beta-unsaturated thioesterswere produced in moderate to high yields with very good functionalgroup tolerance. This protocol features mild reaction conditions,good substrate scope, and avoids the use of toxic CO gas or odorousthiols, which made it a worthy addition to alpha,beta-unsaturatedthioester synthesis via a thioester transfer process.
引用
收藏
页码:4140 / 4144
页数:5
相关论文
共 50 条
  • [21] Palladium-Catalyzed Synthesis of N-Aryl Carbamates
    Vinogradova, Ekaterina V.
    Park, Nathaniel H.
    Fors, Brett P.
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2013, 15 (06) : 1394 - 1397
  • [22] Palladium-Catalyzed Synthesis of Aryl and Heteroaryl Difluoromethylated Phosphonates
    Ivanova, Maria V.
    Besset, Tatiana
    Pannecoucke, Xavier
    Poisson, Thomas
    SYNTHESIS-STUTTGART, 2018, 50 (04): : 778 - 784
  • [23] An efficient intermolecular palladium-catalyzed synthesis of aryl ethers
    Torraca, KE
    Huang, XH
    Parrish, CA
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) : 10770 - 10771
  • [24] A palladium-catalyzed synthesis of amidines from aryl halides
    Saluste, C. Gustaf
    Whitby, Richard J.
    Furber, Mark
    Angewandte Chemie (International Edition in English), 2000, 39 (22): : 4156 - 4158
  • [25] GENERAL KETONE SYNTHESIS - REACTION OF ORGANOCOPPER REAGENTS WITH S-ALKYL AND S-ARYL THIOESTERS
    ANDERSON, RJ
    HENRICK, CA
    ROSENBLU.LD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (11) : 3654 - 3655
  • [26] Palladium-Catalyzed Polycondensation for the Synthesis of Poly(Aryl)Sulfides
    Hou, Peng
    Oechsle, Peter
    Kuckling, Dirk
    Paradies, Jan
    MACROMOLECULAR RAPID COMMUNICATIONS, 2020, 41 (10)
  • [27] A palladium-catalyzed synthesis of amidines from aryl halides
    Saluste, CG
    Whitby, RJ
    Furber, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (22) : 4156 - 4158
  • [28] Methods of synthesis -: Palladium-catalyzed formation of aryl amines and aryl eithers
    Höger, S
    CHEMIE IN UNSERER ZEIT, 2001, 35 (02) : 102 - 109
  • [29] Palladium-catalyzed synthesis of aryl sulfides from aryl triflates.
    Zheng, N
    McWilliams, JC
    Fleitz, FJ
    Armstrong, JD
    Volante, RP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U140 - U140
  • [30] Palladium-Catalyzed Synthesis of Aryl Nitriles: Using α-Iminonitrile as Cyano Source for Aryl Halide Cyanations
    Shi, Yu-Long
    Yuan, Qing
    Chen, Zhen-Bang
    Zhang, Fang-Ling
    Liu, Kui
    Zhu, Yong-Ming
    SYNLETT, 2018, 29 (03) : 359 - 363