NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)-H Alkylation of Alkenes

被引：142
|
作者：
Zhou, Fang [1 ]
Zhu, Jin [1 ]
Zhang, Yao [1 ]
Zhu, Shaolin [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 15期
关键词：
alkylation; C-H activation; isomerization; nickel; regioselectivity; SUZUKI CROSS-COUPLINGS; CARBON BOND FORMATION; ROOM-TEMPERATURE; ISOMERIZATION-HYDROBORATION; ASYMMETRIC-SYNTHESIS; ALKYLZINC REAGENTS; GRIGNARD-REAGENTS; NEGISHI REACTIONS; TERTIARY SILANES; NATURAL-PRODUCTS;
D O I：
10.1002/anie.201712731
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The terminal-selective, remote C(sp(3))-H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp(3))-C(sp(3)) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.
引用
收藏
页码：4058 / 4062
页数：5
相关论文
共 50 条
  • [1] Hydroalkylation of unactivated olefins with C(sp3)−H compounds enabled by NiH-catalyzed radical relay
    Shi, Jiang-Ling
    Wang, Youcheng
    Han, Yufeng
    Chen, Jinqi
    Pu, Xiaolan
    Xia, Ying
    [J]. Science Advances, 2024, 10 (51)
  • [2] NiH-catalyzed C(sp3)-Si coupling of alkenes with vinyl chlorosilanes
    Cui, Huanhuan
    Niu, Changhao
    Xing, Mimi
    Zhang, Chun
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (85) : 11989 - 11992
  • [3] Electrochemical NiH-Catalyzed C(sp3)-C(sp3) Coupling of Alkyl Halides and Alkyl Alkenes
    Li, Pengfei
    Kou, Guangsheng
    Feng, Tian
    Wang, Minyan
    Qiu, Youai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (44)
  • [4] NiH-Catalyzed Remote Asymmetric Hydroalkylation of Alkenes with Racemic -Bromo Amides
    Zhou, Fang
    Zhang, Yao
    Xu, Xianfeng
    Zhu, Shaolin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1754 - 1758
  • [5] Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones
    Du, Bingnan
    Ouyang, Yuxin
    Chen, Qishu
    Yu, Wing-Yiu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (37) : 14962 - 14968
  • [6] Terminal-Selective C(sp3)-H Arylation: NiH-Catalyzed Remote Hydroarylation of Unactivated Internal Olefins
    He, Yuli
    Han, Bo
    Zhu, Shaolin
    [J]. ORGANOMETALLICS, 2021, 40 (14) : 2253 - 2264
  • [7] Hydroxoiridium-Catalyzed Hydroalkylation of Terminal Alkenes with Ureas by C(sp3)-H Bond Activation
    Yamauchi, Daisuke
    Nishimura, Takahiro
    Yorimitsu, Hideki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) : 7200 - 7204
  • [8] Terminal C(sp3)-H alkylation of internal alkenes via Ni/H-catalyzed isomerization
    Wang, Zhen-Yu
    Wan, Jia-Hao
    Wang, Gao-Yin
    Wang, Rui
    Jin, Ruo-Xing
    Lan, Quan
    Wang, Xi-Sheng
    [J]. TETRAHEDRON LETTERS, 2018, 59 (23) : 2302 - 2305
  • [9] Hydroxoiridium-Catalyzed sp3 C-H Alkylation of Indoline Derivatives with Terminal Alkenes
    Nakamura, Ikumi
    Yamauchi, Daisuke
    Nishimura, Takahiro
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1347 - 1350
  • [10] Remote sp3 C-H Amination of Alkenes with Nitroarenes
    Xiao, Jichao
    He, Yuli
    Ye, Feng
    Zhu, Shaolin
    [J]. CHEM, 2018, 4 (07): : 1645 - 1657
12345