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
  • [41] SYNTHESIS OF SUBSTITUTED PHENAZINES VIA PALLADIUM-CATALYZED ARYL LIGATION
    Winkler, Jeffrey D.
    Twenter, Barry M.
    Gendrineau, Thomas
    HETEROCYCLES, 2012, 84 (02) : 1345 - 1353
  • [42] PALLADIUM-CATALYZED SYNTHESIS OF UNSYMMETRICAL ALKYL ARYL-PHENYLPHOSPHINATES
    XU, YY
    LI, Z
    XIA, JZ
    GUO, HJ
    HUANG, YZ
    SYNTHESIS-STUTTGART, 1983, (05): : 377 - 378
  • [43] Palladium-catalyzed synthesis of triarylamines from aryl halides and diarylamines
    Yamamoto, T
    Nishiyama, M
    Koie, Y
    TETRAHEDRON LETTERS, 1998, 39 (16) : 2367 - 2370
  • [44] Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides
    Jiang, Huanfeng
    Liu, Bifu
    Li, Yibiao
    Wang, Azhong
    Huang, Huawen
    ORGANIC LETTERS, 2011, 13 (05) : 1028 - 1031
  • [45] Palladium-catalyzed reductive carbonylation of aryl triflates with synthesis gas
    Brenrifuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    SYNLETT, 2007, (16) : 2537 - 2540
  • [46] Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives
    Calcaterra, Andrea
    Fernandez Garcia, Santiago
    Marrone, Federico
    Bernini, Roberta
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    Iazzetti, Antonia
    CATALYSTS, 2024, 14 (07)
  • [47] Synthesis of benzo[C]phenanthridine alkaloids using a palladium-catalyzed aryl-aryl coupling reaction
    Harayama, T
    HETEROCYCLES, 2005, 65 (03) : 697 - 713
  • [48] A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
    Fuwa, Haruhiko
    Mizunuma, Kana
    Matsukida, Seiji
    Sasaki, Makoto
    TETRAHEDRON, 2011, 67 (27-28) : 4995 - 5010
  • [49] An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry
    Brain, CT
    Steer, JT
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17): : 6814 - 6816
  • [50] Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones
    Trongsiriwat, Nisalak
    Li, Minyan
    Pascual-Escudero, Ana
    Yucel, Baris
    Walsh, Patrick J.
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 502 - 509