Copper-Catalyzed Decarboxylative Atom Transfer Radical Addition of Iododifluoroacetate to Alkynyl Carboxylic Acids

被引:70
|
作者
Li, Gang [1 ]
Cao, Yi-Xuan [1 ]
Luo, Chen-Guang [1 ]
Su, Yi-Ming [1 ]
Li, Yan [1 ]
Lan, Quan [1 ]
Wang, Xi-Sheng [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet & Self Assembly Chem Organ Funct, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
H-PHOSPHINE OXIDES; MEDIATED TRIFLUOROMETHYLATION; COUPLING REACTION; TERMINAL ALKYNES; FACILE SYNTHESIS; EFFICIENT; ALKENES; FLUORINE; DIFLUOROMETHYLATION; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.6b02216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of copper-catalyzed decarboxylative atom transfer radical addition of alkynyl carboxylic acids has been developed with a readily available fluoroalkyl halide. This novel protocol has demonstrated a unique difunctionalization of nonterminal alkynes with a broad substrate scope and excellent functional-group tolerance. Mechanistic investigations revealed that the catalytic cycle was initiated by the attack of a difluoroalkyl radical to an in situ generated alkynylcopper species.
引用
收藏
页码:4806 / 4809
页数:4
相关论文
共 50 条
  • [1] Copper-Catalyzed Decarboxylative Disulfonylation of Alkynyl Carboxylic Acids with Sulfinic Acids
    Fu, Hong
    Shang, Jia-Q
    Yang, Tao
    Shen, Yuehai
    Gao, Chuan-Zhu
    Li, Ya-Min
    ORGANIC LETTERS, 2018, 20 (02) : 489 - 492
  • [2] Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles
    Li, Yi
    Shang, Jia-Qi
    Wang, Xiang-Xiang
    Xia, Wen-Jin
    Yang, Tao
    Xin, Yangchun
    Li, Ya-Min
    ORGANIC LETTERS, 2019, 21 (07) : 2227 - 2230
  • [3] Copper-Catalyzed Decarboxylative Cycloaddition of Alkynyl Carboxylic Acids and Sodium Azide with Epoxides and Ethers
    Beukeaw, Danupat
    Yotphan, Sirilata
    CHEMISTRYSELECT, 2021, 6 (36): : 9632 - 9636
  • [4] Copper-catalyzed decarboxylative coupling of aryl halides with alkynyl carboxylic acids performed in water
    Li, Tingyi
    Sun, Peng
    Yang, Hailong
    Zhu, Yan
    Yan, Hong
    Lu, Linhua
    Mao, Jincheng
    TETRAHEDRON, 2012, 68 (32) : 6413 - 6419
  • [5] Highly effective copper-catalyzed decarboxylative coupling of aryl halides with alkynyl carboxylic acids
    Qu, Xiaoming
    Li, Tingyi
    Sun, Peng
    Zhu, Yan
    Yang, Hailong
    Mao, Jincheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) : 6938 - 6942
  • [6] Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides
    Zhao, Dongbing
    Gao, Chao
    Su, Xiaoyu
    He, Yunqing
    You, Jingsong
    Xue, Ying
    CHEMICAL COMMUNICATIONS, 2010, 46 (47) : 9049 - 9051
  • [7] Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids
    Lim, Jeongah
    Choi, Jinseop
    Kim, Han-Sung
    Kim, In Seon
    Nam, Kye Chun
    Kim, Jimin
    Lee, Sunwoo
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 303 - 308
  • [8] Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
    Stanton, Michael P.
    Hoover, Jessica M.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (03): : 1713 - 1719
  • [9] Copper-Catalyzed Decarboxylative Sulfonylation of α,β-Unsaturated Carboxylic Acids
    Rokade, Balaji V.
    Prabhu, Kandikere Ramaiah
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8110 - 8117
  • [10] Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids
    Yi, Ji-Tao
    Zhou, Xiang
    Chen, Qi-Long
    Chen, Zhi-Da
    Lu, Gui
    Weng, Jiang
    CHEMICAL COMMUNICATIONS, 2022, 58 (67) : 9409 - 9412