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
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 64期
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
    Gilbert J. Choi
    Qilei Zhu
    David C. Miller
    Carol J. Gu
    Robert R. Knowles
    Nature, 2016, 539 : 268 - 271
  • [2] 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
  • [3] Proton-coupled electron transfer in organic synthesis and asymmetric catalysis
    Knowles, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [4] Proton-coupled electron transfer in organic synthesis and asymmetric catalysis
    Knowles, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [5] 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
  • [6] Oxidative lactonization of C(sp3)-H bond in methyl aromatic alcohols enabled by proton-coupled electron transfer
    Shanyi Chen
    Qihong Lai
    Chao Liu
    Hui Liu
    Mingqiang Huang
    Shunyou Cai
    Science China Chemistry, 2022, 65 : 1526 - 1531
  • [7] 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
  • [8] Insights into the Role of Graphitic Carbon Nitride as a Photobase in Proton-Coupled Electron Transfer in (sp3)C-H Oxygenation of Oxazolidinones
    Galushchinskiy, Alexey
    Zou, Yajun
    Odutola, Jokotadeola
    Nikacevic, Pavle
    Shi, Jian-Wen
    Tkachenko, Nikolai
    Lopez, Nuria
    Farras, Pau
    Savateev, Oleksandr
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (18)
  • [9] 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
  • [10] Photocatalytic Alkylation of C(sp3)-H Bonds Using Sulfonylhydrazones
    Pulcinella, Antonio
    Bonciolini, Stefano
    Lukas, Florian
    Sorato, Andrea
    Noel, Timothy
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (03)
12345