Cobalt-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Diarylmanganese Reagents with Secondary Alkyl Iodides

被引：16
|
作者：
Hofmayer, Maximilian S. [1 ]
Hammann, Jeffrey M. [1 ]
Haas, Diana [1 ]
Knochel, Paul [1 ]
机构：
[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 24期
关键词：
ARYL GRIGNARD-REAGENTS; C-H ACTIVATION; 1,4-COBALT MIGRATION; (HETERO)ARYLZINC REAGENTS; ARYLMAGNESIUM REAGENTS; CYCLIC HALOHYDRINS; ORGANIC HALIDES; BROMIDES; DERIVATIVES; CHLORIDES;
D O I：
10.1021/acs.orglett.6b03349
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cobalt-catalyzed cross-coupling of diarylmanganese reagents with secondary alkyl iodides using the THF-soluble salt CoCl2. 2LiCl, which leads to the cross-coupling products in up to 92% yield, is reported. High diastereoselectivities can be reached in these cross-couplings (dr up to 99:1). Remarkably, rearrangement of secondary alkyl iodides to unbranched products was not observed in these C-C forming reactions.
引用
收藏
页码：6456 / 6459
页数：4
相关论文
共 50 条
  • [21] Cobalt-Catalyzed Twofold Direct C(sp2)-C(sp3) Bond Coupling: Regioselective C-3 Alkylation of Coumarins with (Cyclo)alkyl Ethers
    Dian, Longyang
    Zhao, Hui
    Zhang-Negrerie, Daisy
    Du, Yunfei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2422 - 2426
  • [22] Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reaction between Unactivated C(sp2)-H and C(sp3)-H Bonds
    Li, Qun
    Hu, Weipeng
    Hu, Renjian
    Lu, Hongjian
    Li, Guigen
    [J]. ORGANIC LETTERS, 2017, 19 (17) : 4676 - 4679
  • [23] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Chlorobenzamides with Alkyl Grignard Reagents: Development of Catalyst System, Synthetic Scope, and Application
    Bisz, Elwira
    Szostak, Michal
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) : 85 - 95
  • [24] Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds
    Dong, Xunqing
    Li, Qun
    Li, Guigen
    Lu, Hongjian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13402 - 13413
  • [25] Cobalt-Catalyzed Negishi Cross-Coupling Reactions of (Hetero)Arylzinc Reagents with Primary and Secondary Alkyl Bromides and Iodides
    Hammann, Jeffrey M.
    Haas, Diana
    Knochel, Paul
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (15) : 4478 - 4481
  • [26] Nickel-Catalyzed Electrochemical C(sp3)-C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
    Luo, Jian
    Hu, Bo
    Wu, Wenda
    Hu, Maowei
    Liu, T. Leo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 6107 - 6116
  • [27] Ni-catalyzed C(sp2)-carbon and C(sp2)-heteroatom cross-coupling reactions
    Li, Z
    Fu, Y
    Liu, L
    Guo, QX
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (12) : 1508 - 1529
  • [28] Nitrimines as Reagents for Metal-Free Formal C(sp2)-C(sp2) Cross-Coupling Reactions
    Angeles-Dunham, Veronica V.
    Nickerson, David M.
    Ray, Devin M.
    Mattson, Anita E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14538 - 14541
  • [29] Nickel-Catalyzed Cross-Coupling of Alkyl Zinc Halides for the Formation of C(sp2)-C(sp3) Bonds: Scope and Mechanism
    Phapale, Vilas B.
    Guisan-Ceinos, Manuel
    Bunuel, Elena
    Cardenas, Diego J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) : 12681 - 12688
  • [30] Palladium-Catalyzed C(sp3)-Si Bonds Transformation for Constructing Trifluoropropyl (Hetero)arenes through C(sp3)-C(sp2) Cross-Coupling Reactions
    Liu Junjun
    Lu Taotao
    Ma Ping
    Zhao Qingyang
    Yee, Kwong Fuk
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1319 - 1326
12345