Branch-Selective Hydroarylation: Iodoarene-Olefin Cross-Coupling

被引：198
作者：
Green, Samantha A. [1 ]
Matos, Jeishla L. M. [1 ]
Yagi, Akiko [1 ]
Shenvi, Ryan A. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 39期
关键词：
HYDROGEN-ATOM TRANSFER; COBALT-CARBON BONDS; UNACTIVATED OLEFINS; CATALYZED HYDROARYLATION; ALKENE HYDROARYLATION; ALKYL-HALIDES; VINYL ETHERS; CO-CATALYSIS; HYDROFLUORINATION; MECHANISMS;
D O I：
10.1021/jacs.6b08507
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A combination of cobalt and nickel catalytic cycles enables a highly branch-selective (Markovnikov) olefin hydroarylation. Radical cyclization and ring scission experiments are consistent with hydrogen atom transfer (HAT) generation of a carbon-centered radical that leads to engagement of a nickel cycle.
引用
收藏
页码：12779 / 12782
页数：4
相关论文
共 74 条
  • [11] Branch-Selective, Iridium-Catalyzed Hydroarylation of Monosubstituted Alkenes via a Cooperative Destabilization Strategy
    Crisenza, Giacomo E. M.
    McCreanor, Niall G.
    Bower, John F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) : 10258 - 10261
  • [12] Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins
    Crossley, Steven W. M.
    Obradors, Carla
    Martinez, Ruben M.
    Shenvi, Ryan A.
    [J]. CHEMICAL REVIEWS, 2016, 116 (15) : 8912 - 9000
  • [13] Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol
    Crossley, Steven W. M.
    Martinez, Ruben M.
    Guevara-Zuluaga, Sebastian
    Shenvi, Ryan A.
    [J]. ORGANIC LETTERS, 2016, 18 (11) : 2620 - 2623
  • [14] Simple, Chemoselective, Catalytic Olefin Isomerization
    Crossley, Steven W. M.
    Barabe, Francis
    Shenvi, Ryan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (48) : 16788 - 16791
  • [15] Hydromethylation of Unactivated Olefins
    Dao, Hai T.
    Li, Chao
    Michaudel, Quentin
    Maxwell, Brad D.
    Baran, Phil S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) : 8046 - 8049
  • [16] Synthesis and Potent Antimalarial Activity of Kalihinol B
    Daub, Mary Elisabeth
    Prudhomme, Jacques
    Le Roch, Karine
    Vanderwal, Christopher D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) : 4912 - 4915
  • [17] Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
    Dreher, Spencer D.
    Dormer, Peter G.
    Sandrock, Deidre L.
    Molander, Gary A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9257 - +
  • [18] Iridium-Catalyzed Branch-Selective Hydroarylation of Vinyl Ethers via C-H Bond Activation
    Ebe, Yusuke
    Nishimura, Takahiro
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) : 5899 - 5902
  • [19] EISENBERG DC, 1991, ISR J CHEM, V31, P55
  • [20] Mechanistic Basis for High Stereoselectivity and Broad Substrate Scope in the (salen)Co(III)-Catalyzed Hydrolytic Kinetic Resolution
    Ford, David D.
    Nielsen, Lars P. C.
    Zuend, Stephan J.
    Musgrave, Charles B.
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (41) : 15595 - 15608
12345678