Iridium-Catalyzed Site- and Enantioselective C(sp2)-H Borylation of Benzhydryl Ethers: Enantioselectivity Amplification by Kinetic Resolution Relay

被引：7
|
作者：
Jing, Ke [1 ,2 ]
Chen, Lili [1 ]
Zhang, Panke [2 ]
Xu, Senmiao [1 ]
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[2] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Henan, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Asymmetric catalysis; Benzhydryl ethers; C-H activation; Enantioselectivity; Kinetic resolution; C-H OLEFINATION; ACTIVATION; IODINATION; ARENES; BONDS; ACIDS;
D O I：
10.1002/cjoc.202300161
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Comprehensive SummaryWe herein report a simple ether-directed iridium-catalyzed site- and enantioselective C(sp(2))-H borylation of benzhydryl ethers for the first time. Various chiral benzhydryl ethers were obtained with high enantioselectivities in the presence of a tailor-made chiral bidentate boryl ligand. We found that the kinetic resolution relay significantly amplified the enantioselectivity. The synthetic utility of the current method was demonstrated by gram-scale C-H borylation and C-B bond transformations.
引用
收藏
页码：2119 / 2124
页数：6
相关论文
共 50 条
  • [1] Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Aminocyclopropanes
    Shi, Yongjia
    Yang, Yuhuan
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (19)
  • [2] Iridium-Catalyzed Enantioselective C-H Borylation of Diarylphosphinates
    Song, Shu-Yong
    Li, Yinwu
    Ke, Zhuofeng
    Xu, Senmiao
    ACS CATALYSIS, 2021, 11 (21) : 13445 - 13451
  • [3] Iridium-Catalyzed Enantioselective α-C(sp3)-H Borylation of Azacycles
    Chen, Lili
    Yang, Yuhuan
    Liu, Luhua
    Gao, Qian
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (28) : 12062 - 12068
  • [4] Iridium-Catalyzed Enantioselective Unbiased Methylene C(sp3)-H Borylation of Acyclic Amides
    Yang, Yuhuan
    Chen, Lili
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (07) : 3524 - 3528
  • [5] Diastereodivergent Parallel Kinetic Resolution of Racemic 2-Substituted Pyrrolidines via Iridium-Catalyzed C(sp 3)-H Borylation
    He, Maosheng
    Xie, Liang-Jun
    Chen, Lili
    Xu, Senmiao
    ACS CATALYSIS, 2024, 14 (24): : 18701 - 18707
  • [6] Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective Iridium-Catalyzed C-H Borylation
    Song, Peidong
    Hu, Linlin
    Yu, Tao
    Jiao, Jiao
    He, Yangqing
    Xu, Liang
    Li, Pengfei
    ACS CATALYSIS, 2021, 11 (12) : 7339 - 7349
  • [7] Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Asymmetric C(sp2)-H Borylation of Diarylmethylamines
    Zou, Xiaoliang
    Zhao, Haonan
    Li, Yinwu
    Gao, Qian
    Ke, Zhuofeng
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) : 5334 - 5342
  • [8] Iridium-Catalyzed β-C(sp2)-H Borylation of Enamides - Access to 3,3-Dihalogeno-2-methoxypiperidines
    Gillaizeau, Isabelle
    Dondasse, Ismael
    Nicolas, Cyril
    Mimoun, Liliane
    Sukach, Volodymyr
    Meudal, Herve
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (02)
  • [9] Iridium-Catalyzed Borylation of Secondary C-H Bonds in Cyclic Ethers
    Liskey, Carl W.
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12422 - 12425
  • [10] Iridium-Catalyzed Site-Selective C-H Borylation of 2-Pyridones
    Miura, Wataru
    Hirano, Koji
    Miura, Masahiro
    SYNTHESIS-STUTTGART, 2017, 49 (21): : 4745 - 4752
12345