Nickel-Catalyzed Reductive Cross-Coupling of (Hetero)aryl Halides with 2-Chloro-1,1-difluoroethane: Facile Access to 2,2-Difluoroethylated Aromatics

被引:6
作者
Diao, Zhengzhen [1 ]
Feng, Yu [1 ]
Zhang, Jida [1 ]
Wang, Xin [2 ]
Li, Hansheng [2 ]
Ding, Chen [2 ]
Zhou, Zhen [1 ]
Li, Xinjin [1 ,3 ]
机构
[1] Shandong Univ Technol, Sch Chem & Chem Engn, 266 West Xincun Rd, Zibo 255000, Peoples R China
[2] Dongyue Fluorosilicone Technol Grp, State Key Lab Fluorinated Funct Membrane Mat, Zibo 256400, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
aryl halides; 2; 2-difluoroethylation; fluorine; nickel; reductive coupling; BACE1; INHIBITORS; ALKYL-HALIDES; DIFLUOROMETHYLATION; FLUORINE; BROMIDES; MILD; 2,2-DICHLORO-1,1,1-TRIFLUOROETHANE; PHARMACEUTICALS; ALDEHYDES; CHLORIDES;
D O I
10.1002/ajoc.202200169
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient nickel-catalyzed 2,2-difluoroethylation of (hetero)aryl halides with readily available 2-chloro-1,1-difluoroethane has been developed. The reductive cross-coupling reaction is synthetically simple and exhibits good functional group tolerance. This approach provides a facile access to synthesize 2,2-difluoroethylated molecules for drug discovery.
引用
收藏
页数:5
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共 63 条
  • [1] [Anonymous], 2018, ANGEW CHEM, DOI DOI 10.1002/ANIE.201803228
  • [2] Begue J.-P., 2008, BIOORGAN MED CHEM, P1
  • [3] (α-monofluoroalkyl)phosphonates:: a class of isoacidic and "tunable" mimics of biological phosphates
    Berkowitz, DB
    Bose, M
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (01) : 13 - 33
  • [4] A MILD, CONVENIENT, HALOGEN-EXCHANGE ROUTE TO GEM-DIFLUORIDES AND TRIFLUORIDES
    BLOODWORTH, AJ
    BOWYER, KJ
    MITCHELL, JC
    [J]. TETRAHEDRON LETTERS, 1987, 28 (44) : 5347 - 5350
  • [5] Nickel-catalyzed reductive monofluoroakylation of alkyl tosylate with bromofluoromethane to primary alkyl fluoride
    Cui, Ru
    Sheng, Jie
    Wu, Bing-Bing
    Hu, Duo-Duo
    Zheng, Hong-Qian
    Wang, Xi-Sheng
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (72) : 9084 - 9087
  • [6] Preparation of 1,1-difluoroalkanes from aldehydes via 1,1-bistriflates: Advantageous use of HF-Lewis base reagents
    Dolbier, William R., Jr.
    Okamoto, Masamune
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2014, 167 : 96 - 100
  • [7] Anomalous elimination of HCl from 2-chloro-1,1-difluoroethane. Likely involvement of a 1,2-FCI interchange mechanism
    Dolbier, WR
    Romelaer, R
    Baker, JM
    [J]. TETRAHEDRON LETTERS, 2002, 43 (45) : 8075 - 8077
  • [8] Cross-Electrophile Coupling: Principles of Reactivity and Selectivity
    Everson, Daniel A.
    Weix, Daniel J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) : 4793 - 4798
  • [9] Feng Z, 2017, NAT CHEM, V9, P918, DOI [10.1038/NCHEM.2746, 10.1038/nchem.2746]
  • [10] Nickel-Catalyzed Difluoromethylation of (Hetero)aryl Bromides with BrCF2H
    Gao, Xing
    He, Xu
    Zhang, Xingang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 215 - 222