Asymmetric alkylation of remote C(sp3)-H bonds by combining proton-coupled electron transfer with chiral Lewis acid catalysis

被引:100
|
作者
Yuan, Wei [1 ]
Zhou, Zijun [1 ]
Gong, Lei [1 ]
Meggers, Eric [1 ,2 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[2] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany
基金
中国国家自然科学基金;
关键词
C-H BONDS; PHOTOREDOX CATALYSIS; ACTIVATION; FUNCTIONALIZATION; RADICALS; AMINATION; STRATEGY; COMPLEX; IODINE;
D O I
10.1039/c7cc04941b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic asymmetric alkylation of the remote, unactivated delta-position of N-alkyl amides was enabled by the combination of visible-light-induced proton-coupled electron transfer, 1,5-hydrogen atomtransfer, and chiral Lewis acid catalysis in up to 82% yield and up to 97% ee.
引用
收藏
页码:8964 / 8967
页数:4
相关论文
共 50 条
  • [1] Catalytic alkylation of remote C-H bonds enabled by proton-coupled electron transfer
    Choi, Gilbert J.
    Zhu, Qilei
    Miller, David C.
    Gu, Carol J.
    Knowles, Robert R.
    NATURE, 2016, 539 (7628) : 268 - 271
  • [2] Oxidative lactonization of C(sp3)-H bond in methyl aromatic alcohols enabled by proton-coupled electron transfer
    Chen, Shanyi
    Lai, Qihong
    Liu, Chao
    Liu, Hui
    Huang, Mingqiang
    Cai, Shunyou
    SCIENCE CHINA-CHEMISTRY, 2022, 65 (08) : 1526 - 1531
  • [3] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
  • [4] Enantioselective alkylation of α-amino C(sp3)-H bonds via photoredox and nickel catalysis
    Li, Jian
    Cheng, Buqing
    Shu, Xiaomin
    Xu, Zhen
    Li, Chengyang
    Huo, Haohua
    NATURE CATALYSIS, 2024, 7 (08): : 889 - 899
  • [5] Directed γ-C(sp3)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis
    Chen, Dian-Feng
    Chu, Tjohn C. K.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) : 14897 - 14900
  • [6] Surgical Cleavage of Unstrained C(sp3)-C(sp3) Bonds in General Alcohols for Heteroaryl C-H Alkylation and Acylation
    Wang, Yaxin
    Yang, Le
    Liu, Shuai
    Huang, Lixia
    Liu, Zhong-Quan
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) : 4568 - 4574
  • [7] Visible-light promoted regioselective amination and alkylation of remote C(sp3)-H bonds
    Guo, Quanping
    Peng, Qiang
    Chai, Hongli
    Huo, Yumei
    Wang, Shan
    Xu, Zhaoqing
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [8] Selective Bromination of sp3 C ∼ H Bonds by Organophotoredox Catalysis
    Kee, Choon Wee
    Chan, Ke Min
    Wong, Ming Wah
    Tan, Choon-Hong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) : 536 - 544
  • [9] Amidyl Radical Directed Remote Allylation of Unactivated sp3 C-H Bonds by Organic Photoredox Catalysis
    Wu, Kui
    Wang, Lushun
    Colon-Rodriguez, Sonivette
    Flechsig, Gerd-Uwe
    Wang, Ting
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1774 - 1778
  • [10] Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp3)-H bonds
    Wen, Xin
    Wang, Yong
    Zhang, X. Peter
    CHEMICAL SCIENCE, 2018, 9 (22) : 5082 - 5086