Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides

被引：2
|
作者：
Pages, Lucas [1 ]
Bouquin, Maxime [1 ]
Jaroschik, Florian [1 ]
Monnier, Florian [1 ]
Taillefer, Marc [1 ]
机构：
[1] Univ Montpellier, ICGM, CNRS, ENSCM, F-34095 Montpellier, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 02期
关键词：
THIOL-ENE CLICK; THIYL RADICALS; ALLENES; HYDROAMINATION; BENZENETHIOL; CONSTRUCTION; ADDITIONS;
D O I：
10.1021/acs.joc.2c02716
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a simple protocol for the copper-catalyzed hydrothiolation of N-unsaturated precursors, i.e., allenamides, enamides, and ynamides, under mild conditions. This method proceeds with a low loading of a commercially available Cu(CH3CN)(4)PF6 catalyst and enables the room-temperature transformation of a wide range of aromatic and aliphatic thiols into allylic or vinylic thioethers, 1,3-dithioethers, and thioaminals with good regio- and stereoselectivity.
引用
收藏
页码：1168 / 1176
页数：9
相关论文
共 50 条
  • [1] Copper-Catalyzed Regio- and Stereoselective Hydroarylation of Ynamide
    Maity, Avijit
    Sahoo, Akhila K.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 852 - 863
  • [2] Copper-Catalyzed Regio- and Stereoselective Aminoboration of Alkenylboronates
    Nishikawa, Daiki
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2016, 18 (19) : 4856 - 4859
  • [3] Copper-catalyzed regio- and stereoselective fluorocarboalkynylation of alkynes
    Zhao, Binlin
    Zheng, Yukun
    Zhu, Tianxiang
    Wang, Mengning
    Wang, Minyan
    Ma, Mengtao
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6857 - 6862
  • [4] Regio- and Stereoselective Synthesis of Multisubstituted Enamides by Treatment of Ynamides with Boronic Acids
    Tahara, Atsushi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (07) : 749 - 750
  • [5] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [6] Regio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron
    Thorpe, Steven B.
    Guo, Xi
    Santos, Webster L.
    CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 424 - 426
  • [7] Copper-Catalyzed Regio- and Stereoselective O-Arylation of Enolates
    Xu, Ze-Feng
    Cai, Chen-Xin
    Jiang, Min
    Liu, Jin-Tao
    ORGANIC LETTERS, 2014, 16 (13) : 3436 - 3439
  • [8] Regio- and Stereoselective Synthesis of Tri- and Tetrasubstituted Enamides via Palladium-Catalyzed Silaboration of Ynamides
    Saito, Nozomi
    Saito, Keiichi
    Sato, Hiroyasu
    Sato, Yoshihiro
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 853 - 856
  • [9] Regio- and Stereoselective Hydrophosphorylation of Ynamides: A Facile Approach to (Z)-β-Phosphor-Enamides
    Peng, Zhiyuan
    Zhang, Zhenming
    Zeng, Xianzhu
    Tu, Yongliang
    Zhao, Junfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) : 4489 - 4494
  • [10] Regio- and stereoselective copper-catalyzed carbozincation reactions of alkynyl sulfoximines and sulfones
    Sklute, Genia
    Bolm, Carsten
    Marek, Ilan
    ORGANIC LETTERS, 2007, 9 (07) : 1259 - 1261
12345