Cobalt-catalyzed nucleophilic addition of the allylic C(sp3)-H bond of simple alkenes to ketones

被引:12
|
作者
Mita, Tsuyoshi [1 ]
Uchiyama, Masashi [1 ]
Michigami, Kenichi [1 ]
Sato, Yoshihiro [1 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源
关键词
alkenes; C-H activation; C(sp(3))-H bonds; cobalt; ketones; CARBOXYLATION; FUNCTIONALIZATION; OLEFINS; ACTIVATION; ALLYLATION; COMPLEXES; OXIDATION; UMPOLUNG;
D O I
10.3762/bjoc.14.176
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We herein describe a cobalt/Xantphos-catalyzed regioselective addition of simple alkenes to acetophenone derivatives, affording branched homoallylic alcohols in high yields with perfect branch selectivities. The intermediate of the reaction would be a nucleophilic allylcobalt(I) species generated via cleavage of the low reactive allylic C(sp(3))-H bond of simple terminal alkenes.
引用
收藏
页码:2012 / 2017
页数:6
相关论文
共 50 条
  • [1] Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)-H bonds
    Ren, Tian-Lu
    Xu, Bao-Hua
    Mahmood, Sajid
    Sun, Ming-Xue
    Zhang, Suo-Jiang
    TETRAHEDRON, 2017, 73 (20) : 2943 - 2948
  • [2] Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO2
    Michigami, Kenichi
    Mita, Tsuyoshi
    Sato, Yoshihiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (17) : 6094 - 6097
  • [3] Cobalt-catalyzed C(sp3)-H bond functionalization to access indole derivatives
    Zhang, He
    Yang, Dandan
    Zhao, Xiao-Fang
    Niu, Jun-Long
    Song, Mao-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (14) : 3723 - 3729
  • [4] Co-Catalyzed Direct Addition of Allylic C(sp3)-H Bonds to Ketones
    Mita, Tsuyoshi
    Hanagata, Satoshi
    Michigami, Kenichi
    Sato, Yoshihiro
    ORGANIC LETTERS, 2017, 19 (21) : 5876 - 5879
  • [5] Cobalt-Catalyzed C(sp3)-H Functionalization Reactions
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1193 - 1205
  • [6] Allylic C(sp3)-C(sp3) Bond Formation Through Pd-Catalyzed C(sp3)-H Activation of Alkenes and 1,4-Dienes
    Muzart, Jacques
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2268 - 2288
  • [7] Manganese/cobalt-catalyzed oxidative C(sp3)-H/C(sp3)-H coupling: a route to α-tertiary β-arylethylamines
    Tan, Meiling
    Li, Kaizhi
    Yin, Jiangliang
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2018, 54 (10) : 1221 - 1224
  • [8] Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes via C(sp3)-H bond activation of 8-methylquinoline
    Tan, Heng
    Khan, Ruhima
    Xu, Dandan
    Zhou, Yongyun
    Zhang, Xuexin
    Shi, Guangrui
    Fan, Baomin
    CHEMICAL COMMUNICATIONS, 2020, 56 (83) : 12570 - 12573
  • [9] The recent advances in cobalt-catalyzed C(sp3)-H functionalization reactions
    Desai, Bhargav
    Uppuluru, Ajay
    Dey, Ashutosh
    Deshpande, Neha
    Dholakiya, Bharatkumar Z.
    Sivaramakrishna, Akella
    Naveen, Togati
    Padala, Kishor
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (04) : 673 - 699
  • [10] Iron- and cobalt-catalyzed C(sp3)-H bond functionalization reactions and their application in organic synthesis
    Liu, Yungen
    You, Tingjie
    Wang, Hai-Xu
    Tang, Zhou
    Zhou, Cong-Ying
    Che, Chi-Ming
    CHEMICAL SOCIETY REVIEWS, 2020, 49 (15) : 5310 - 5358