Copper-Catalyzed Geminal Difunctionalization of Terminal Alkynes by Splitting Sulfonyl Hydrazones into Two Parts

被引:33
作者
Sun, Qi
Li, Linge
Liu, Liyan
Guan, Qianqian
Yang, Yu
Zha, Zhenggen
Wang, Zhiyong [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
关键词
VINYL SULFONES; N-TOSYLHYDRAZONES; (E)-VINYL SULFONES; STEREOSELECTIVE-SYNTHESIS; CINNAMIC-ACIDS; SULFUR-DIOXIDE; BOND FORMATION; RADICAL-ADDITION; INHIBITORS; EFFICIENT;
D O I
10.1021/acs.orglett.8b02268
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper(I)-catalyzed geminal difunctionalization of terminal alkynes was developed via a carbene migratory insertion and an addition of a sulfonyl anion to the triple bond at the same time under mild reaction conditions, providing a variety of vinyl sulfones with good yields and excellent stereoselectivities.
引用
收藏
页码:5592 / 5596
页数:5
相关论文
共 60 条
  • [11] Fan W, 2016, ORG CHEM FRONT, V3, P1493
  • [12] An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation
    Fan, Weizheng
    Su, Jiapeng
    Shi, Dongyang
    Feng, Bainian
    [J]. TETRAHEDRON, 2015, 71 (38) : 6740 - 6743
  • [13] Vinyl sulfones:: Inhibitors of SrtA, a transpeptidase required for cell wall protein anchoring and virulence in Staphylococcus aureus
    Frankel, BA
    Bentley, M
    Kruger, RG
    McCafferty, DG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3404 - 3405
  • [14] MULTIPLY CONVERGENT SYNTHESES VIA CONJUGATE-ADDITION REACTIONS TO CYCLOALKENYL SULFONES
    FUCHS, PL
    BRAISH, TF
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 903 - 917
  • [15] Copper-Catalyzed Difunctionalization of Terminal Alkynes with Diazo Esters and Amines to Construct -Enamino Esters
    Gao, Bao
    Huang, Hanmin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) : 4075 - 4084
  • [16] NBS-promoted halosulfonylation of terminal alkynes: highly regio- and stereoselective synthesis of (E)-β-halo vinylsulfones
    Gao, Yang
    Wu, Wanqing
    Huang, Yubing
    Huang, Kefan
    Jiang, Huanfeng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (04): : 361 - 364
  • [17] Nickel-Catalyzed Intermolecular Carbosulfonylation of Alkynes via Sulfonyl Radicals
    Garcia-Dominguez, Andres
    Mueller, Simona
    Nevado, Cristina
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (33) : 9949 - 9952
  • [18] Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent
    Kadari, Lingaswamy
    Palakodety, Radha Krishna
    Yallapragada, Lakshmi Prapurna
    [J]. ORGANIC LETTERS, 2017, 19 (10) : 2580 - 2583
  • [19] Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications
    Krautwald, Simon
    Bezdek, Mate J.
    Chirik, Paul J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (10) : 3868 - 3875
  • [20] Copper-Catalyzed Aerobic Oxidative Transformation of Ketone-Derived N-Tosyl Hydrazones: An Entry to Alkynes
    Li, Xianwei
    Liu, Xiaohang
    Chen, Huoji
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14485 - 14489