Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes

被引：34
|
作者：
Ye, Changqing [1 ]
Li, Yajun [1 ]
Bao, Hongli [1 ]
机构：
[1] Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Key Lab Coal Ethylene Glycol & Its Related Techno, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 21期
关键词：
Copper-catalysis; Alkylation; Sonogashira coupling; Decarboxylation; CROSS-COUPLING REACTIONS; LIGHT PHOTOREDOX CATALYSIS; ALPHA-AMINO-ACIDS; C-H BONDS; VISIBLE-LIGHT; GRIGNARD-REAGENTS; SONOGASHIRA REACTIONS; C(SP(3))-H BONDS; HALIDES; BROMIDES;
D O I：
10.1002/adsc.201700798
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A copper-catalyzed decarboxylative alkylation of terminal alkynes under mild reaction conditions has been reported. Various alkyl diacyl peroxides were applied as the alkyl source for the formation of C(sp(3))-C(sp) bond. A range of terminal alkynes including aryl alkynes and alkyl alkynes delivered the alkylated internal alkynes with good to high performances. Mechanism studies suggested that this reaction involves a free radical pathway.
引用
收藏
页码：3720 / 3724
页数：5
相关论文
共 50 条
  • [31] COPPER-CATALYZED COUPLING REACTION OF ARYL AND VINYL HALIDES WITH TERMINAL ALKYNES
    OKURO, K
    FURUUNE, M
    MIURA, M
    NOMURA, M
    TETRAHEDRON LETTERS, 1992, 33 (37) : 5363 - 5364
  • [32] N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates
    Jin, Liqun
    Hao, Wangfang
    Xu, Jianeng
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    Mo, Weimin
    Hu, Xinquan
    CHEMICAL COMMUNICATIONS, 2017, 53 (29) : 4124 - 4127
  • [33] Copper-Catalyzed Decarboxylative Trifluoromethylation of Allylic Bromodifluoroacetates
    Ambler, Brett R.
    Altman, Ryan A.
    ORGANIC LETTERS, 2013, 15 (21) : 5578 - 5581
  • [34] Copper-catalyzed stereoselective alkylhydrazination of alkynes
    Lei, Jian
    Gao, Huaxin
    Huang, Miaoling
    Liu, Xiao
    Mao, Yangfan
    Xie, Xiaolan
    CHEMICAL COMMUNICATIONS, 2020, 56 (06) : 920 - 923
  • [35] Copper-Catalyzed Twofold Silylmetalation of Alkynes
    Yamagishi, Hiroki
    Shimokawa, Jun
    Yorimitsu, Hideki
    SYNLETT, 2019, 30 (13) : 1551 - 1554
  • [36] Copper-Catalyzed Azidative Multifunctionalization of Alkynes
    Zheng, Guangfan
    Sun, Jiaqiong
    Liu, Yang
    Yang, Shengbiao
    Li, Yan
    Sun, Haizhu
    Zhang, Qian
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12813 - 12820
  • [37] Copper-catalyzed decarboxylative trifluoroethylation of cinnamic acids
    Zhang, Yun
    Du, Hongli
    Zhu, Mingxiang
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2017, 58 (09) : 880 - 883
  • [38] Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates
    Ambler, Brett R.
    Peddi, Santosh
    Altman, Ryan A.
    SYNTHESIS-STUTTGART, 2014, 46 (14): : 1938 - 1946
  • [39] Copper-catalyzed Markovnikov hydration of alkynes
    Hassam, Mohammad
    Li, Wen-Shan
    TETRAHEDRON, 2015, 71 (18) : 2719 - 2723
  • [40] Copper-Catalyzed Silylcupration of Activated Alkynes
    Vercruysse, Sebastien
    Jouvin, Kevin
    Riant, Olivier
    Evano, Gwilherm
    SYNTHESIS-STUTTGART, 2016, 48 (19): : 3373 - 3381
12345