Simple Ether-Directed Enantioselective C(sp3) H Borylation of Cyclopropanes Enabled by Iridium Catalysis

被引：18
|
作者：
Xie, Tian [1 ,2 ]
Chen, Lili [2 ]
Shen, Zhenlu [1 ]
Xu, Senmiao [2 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 14期
基金：
中国国家自然科学基金; 国家重点研发计划;
关键词：
Asymmetric Catalysis; C-H Borylation; Chiral Bidentate Boryl Ligand; Cyclopropane; Synthetic Method; SIMMONS-SMITH REACTION; ALLYLIC ALCOHOLS; FUNCTIONALIZATION; SILYLATION; ACTIVATION; ACCESS;
D O I：
10.1002/anie.202300199
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reported here is an efficient and simple ether-directed iridium-catalyzed enantioselective C(sp(3)) H borylation of cyclopropanes. Various functional groups were well-tolerated, affording a vast array of chiral cyclopropanes with high enantioselectivities. We also demonstrated that the turnover numbers of the current reaction could be up to 335.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Copper-Mediated Dehydrogenative C(sp3)-H Borylation of Alkanes
    Sang, Ruocheng
    Han, Wangyujing
    Zhang, Hanwen
    Saunders, Carla M.
    Noble, Adam
    Aggarwal, Varinder K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (28) : 15207 - 15217
  • [32] Intermolecular Enantioselective Benzylic C(sp3)-H Amination by Cationic Copper Catalysis
    Dai, Ling
    Chen, Ying-Ying
    Xiao, Li-Jun
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (24)
  • [33] Catalytic Functionalization of Methyl Group on Silicon: Iridium-Catalyzed C(sp3)-H Borylation of Methylchlorosilanes
    Ohmura, Toshimichi
    Torigoe, Takeru
    Suginome, Michinori
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17416 - 17419
  • [34] Chiral Bidentate Boryl Ligand-Enabled Iridium-Catalyzed Enantioselective Dual C-H Borylation of Ferrocenes: Reaction Development and Mechanistic Insights
    Zou, Xiaoliang
    Li, Yinwu
    Ke, Zhuofeng
    Xu, Senmiao
    ACS CATALYSIS, 2022, 12 (03) : 1830 - 1840
  • [35] Photoelectrochemical oxidative C(sp3)-H borylation of unactivated hydrocarbons
    Zhong, Ping-Fu
    Tu, Jia-Lin
    Zhao, Yating
    Zhong, Nan
    Yang, Chao
    Guo, Lin
    Xia, Wujiong
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [36] Enantioselective Aerobic Oxidative C(sp3)-H Olefination of Amines via Cooperative Photoredox and Asymmetric Catalysis
    Wei, Guo
    Zhang, Chenhao
    Bures, Filip
    Ye, Xinyi
    Tan, Choon-Hong
    Jiang, Zhiyong
    ACS CATALYSIS, 2016, 6 (06): : 3708 - 3712
  • [37] Photoinduced C(sp3)-H borylation of alkanes mediated by copper(ii) chloride
    Fang, Wen
    Wang, Huai-Qin
    Zhou, Wei
    Luo, Zhi-Wen
    Dai, Jian-Jun
    CHEMICAL COMMUNICATIONS, 2023, 59 (46) : 7108 - 7111
  • [38] Borylation of Unactivated C(sp3)-H Bonds with Bromide as a Traceless Directing Group
    Zhang, Ge
    Li, Meng-Yao
    Ye, Wen-Bo
    He, Zhi-Tao
    Feng, Chen-Guo
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2021, 23 (08) : 2948 - 2953
  • [39] Enantioselective C(sp3)-H bond activation by chiral transition metal catalysts
    Saint-Denis, Tyler G.
    Zhu, Ru-Yi
    Chen, Gang
    Wu, Qing-Feng
    Yu, Jin-Quan
    SCIENCE, 2018, 359 (6377) : 759 - +
  • [40] Ligand-Driven Advances in Iridium-Catalyzed sp3 C-H Borylation: 2,2′-Dipyridylarylmethane
    Jones, Margaret R.
    Schley, Nathan D.
    SYNLETT, 2021, 32 (09) : 845 - 850
12345