Nickel-Catalyzed Cross-Electrophile Coupling Reactions for the Synthesis of gem-Difluorovinyl Arenes

被引：49
作者：
Xiong, Baojian [1 ,2 ,3 ]
Wang, Ting [4 ]
Sun, Haotian [1 ,2 ,3 ]
Li, Yue [1 ,2 ,3 ]
Kramer, Soren [5 ]
Cheng, Gui-Juan [4 ]
Lian, Zhong [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Dermatol, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Hosp, Canc Ctr, Chengdu 610041, Peoples R China
[3] Sichuan Univ, West China Sch Pharm, Chengdu 610041, Peoples R China
[4] Chinese Univ Hong Kong Shenzhen, Sch Life & Hlth Sci, Shenzhen Key Lab Steroid Drug Dev, Warshel Inst Computat Biol, Shenzhen 518172, Peoples R China
[5] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
来源：
ACS CATALYSIS | 2020年 / 10卷 / 22期
关键词：
nickel catalysis; cross-electrophile coupling; gem-difluoroalkenes; 2,2-difluorovinyl tosylate; DFT studies; DIFLUOROMETHYL 2-PYRIDYL SULFONE; LIGHT-EMITTING-DIODES; C-O ACTIVATION; AROMATIC-ALDEHYDES; DIFLUOROALKENES; ALKENES; DIFLUOROOLEFINATION; CONSTRUCTION; AMIDATION; HALIDES;
D O I：
10.1021/acscatal.0c03993
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A nickel-catalyzed cross-electrophile coupling reaction between (hetero)aryl bromides and 2,2-difluorovinyl tosylate is presented. This protocol provides facile incorporation of the gem-difluorovinyl moiety in organic molecules. The method features mild reaction conditions, good functional group tolerance, and excellent yields. Furthermore, mechanistic experiments and DFT studies indicate a Ni(0)/Ni(II) catalytic cycle, thus differing from the currently accepted catalytic cycle for nickel-catalyzed C(sp(2))-C(sp(2)) cross-electrophile coupling reactions.
引用
收藏
页码：13616 / 13623
页数：8
相关论文
共 82 条
  • [1] Abe T., 2003, CHEM ABSTR, Patent No. 2003042153
  • [2] Abe T., 2003, CHEM ABSTR, Patent No. 2003029211
  • [3] Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates
    Ackerman, Laura K. G.
    Lovell, Matthew M.
    Weix, Daniel J.
    [J]. NATURE, 2015, 524 (7566) : 454 - +
  • [4] SSR182289A, a selective and potent orally active thrombin inhibitor
    Altenburger, JM
    Lassalle, GY
    Matrougui, M
    Galtier, D
    Jetha, JC
    Bocskei, Z
    Berry, CN
    Lunven, C
    Lorrain, J
    Herault, JP
    Schaeffer, P
    O'Connor, SE
    Herbert, JM
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (07) : 1713 - 1730
  • [5] Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes
    Anthony, David
    Lin, Qiao
    Baudet, Judith
    Diao, Tianning
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) : 3198 - 3202
  • [6] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-(2,2-DIFLUOROVINYL)-2'-DEOXYURIDINE
    BOBEK, M
    KAVAI, I
    DECLERCQ, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) : 1494 - 1497
  • [7] Substituted 2,2′-Bipyridines by Nickel Catalysis: 4,4′-Di-tert-butyl-2,2′-bipyridine
    Buonomo, Joseph A.
    Everson, Daniel A.
    Weix, Daniel J.
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (22): : 3099 - 3102
  • [8] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems
    Chelucci, Giorgio
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1344 - 1462
  • [9] A photocatalytic decarboxylative/defluorinative [4+3] annulation of o-hydroxyphenylacetic acids and trifluoromethyl alkenes: synthesis of fluorinated dihydrobenzoxepines
    Chen, Haoguo
    He, Yuwei
    Zhou, Lei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (22): : 3240 - 3244
  • [10] Highly efficient organic light-emitting diodes with a silole-based compound
    Chen, HY
    Lam, WY
    Luo, JD
    Ho, YL
    Tang, BZ
    Zhu, DB
    Wong, M
    Kwok, HS
    [J]. APPLIED PHYSICS LETTERS, 2002, 81 (04) : 574 - 576
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