Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides

被引:11
|
作者
Li, Gang-Jian [1 ]
Pan, You-Lu [1 ]
Liu, Yan-Ling [1 ]
Xu, Hai-Feng [1 ]
Chen, Jian-Zhong [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, 866 Yuhangtang Rd, Hangzhou, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
Sulfinamide; Ni/NHC; Cross-coupling; Methyl sulfinates; ASYMMETRIC-SYNTHESIS; COMPLEXES;
D O I
10.1016/j.tetlet.2019.151260
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Nil NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts
    Zhong, Chuntao
    Tang, Huiling
    Cui, Benqiang
    Shi, Yanhui
    Cao, Changsheng
    RESEARCH ON CHEMICAL INTERMEDIATES, 2022, 48 (10) : 4017 - 4032
  • [22] A novel approach to study catalytic reactions via electrophoretic NMR on the example of Pd/NHC-catalyzed Mizoroki-Heck cross-coupling reaction
    Kulikovskaya, Natalia S.
    Denisova, Ekaterina A.
    Ananikov, Valentine P.
    MAGNETIC RESONANCE IN CHEMISTRY, 2022, 60 (10) : 954 - 962
  • [23] Ni-Catalyzed Desymmetric Radical Cross-Coupling Reaction to Access Axially Chiral Biaryls
    Zhu, Yue-Die
    Dai, Zhen-Yao
    Jiang, Min
    Wang, Pu-Sheng
    ACS CATALYSIS, 2024, 14 (18): : 13860 - 13866
  • [24] α-Unsubstituted Pyrroles by NHC-Catalyzed Three-Component Coupling: Direct Synthesis of a Versatile Atorvastatin Derivative
    Fleige, Mirco
    Glorius, Frank
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (45) : 10773 - 10776
  • [25] Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions
    Cao, Zhi-Chao
    Xie, Si-Jun
    Fang, Huayi
    Shi, Zhang-Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (42) : 13575 - 13579
  • [26] nBu4NI-catalyzed oxidative cross-coupling of carbon dioxide, amines, and aryl ketones: access to O-β-oxoalkyl carbamates
    Peng, Youbin
    Liu, Juan
    Qi, Chaorong
    Yuan, Gaoqing
    Li, Jiawei
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2017, 53 (18) : 2665 - 2668
  • [27] Copper-Catalyzed Radical Cross-Coupling of Oxime Esters and Sulfinates for Synthesis of Cyanoalkylated Sulfones
    Zhou, Xue-Song
    Cheng, Ying
    Chen, Jun
    Yu, Xiao-Ye
    Xiao, Wen-Jing
    Chen, Jia-Rong
    CHEMCATCHEM, 2019, 11 (21) : 5300 - 5305
  • [28] Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides
    Markovic, Tim
    Rocke, Benjamin N.
    Blakemore, David C.
    Mascitti, Vincent
    Willis, Michael C.
    CHEMICAL SCIENCE, 2017, 8 (06) : 4437 - 4442
  • [29] A Ligand-Free Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides
    Ortgies, Dirk H.
    Forgione, Pat
    SYNLETT, 2013, 24 (13) : 1715 - 1721
  • [30] Direct aminoalkylation of arenes and hetarenes via Ni-Catalyzed Negishi cross-coupling reactions
    Melzig, Laurin
    Gavryushin, Andrey
    Knochel, Paul
    ORGANIC LETTERS, 2007, 9 (26) : 5529 - 5532