Benzothiazole-Directed Enantioselective Borylation of Secondary Benzylic C-H Bonds Using Iridium Catalysis

被引:0
|
作者
Xie, Liang-Jun [1 ,2 ]
Chen, Lili [1 ,3 ]
Xu, Senmiao [1 ,3 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 17期
关键词
asymmetric catalysis; borylation; chiral bidentate boryl ligands; C-H activation; synthetic methods; C(SP(3))-H BONDS; FUNCTIONALIZATION;
D O I
10.1055/a-2335-8677
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported here is the iridium-catalyzed regio- and enantio-selective secondary benzylic C-H borylation using benzothiazole as the directing group. Various monosubstituted 2-arylalkylbenzo[d]thiazole were well-tolerated, affording the corresponding products in moderate to good yields with good enantioselectivity. The C-B bond in one borylated product could undergo stereospecific transformations to form aseries of C-C and C-heteroatom bonds.
引用
收藏
页码:2638 / 2647
页数:10
相关论文
共 50 条
  • [21] Selenium-Directed ortho-C-H Borylation by Iridium Catalysis
    Tang, Jia
    Singh, Thishana
    Li, Xingzhen
    Liu, Linpeng
    Zhou, Taigang
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11959 - 11967
  • [22] Directed C-H borylation: From metal catalysis to metal free
    Lu, Jiahang
    Shi, Zhuangzhi
    CHINESE SCIENCE BULLETIN-CHINESE, 2022, 67 (32): : 3823 - 3835
  • [23] Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity
    Larsen, Matthew A.
    Wilson, Conner V.
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) : 8633 - 8643
  • [24] Simple Ether-Directed Enantioselective C(sp3) H Borylation of Cyclopropanes Enabled by Iridium Catalysis
    Xie, Tian
    Chen, Lili
    Shen, Zhenlu
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (14)
  • [25] C-H Borylation by Platinum Catalysis
    Furukawa, Takayuki
    Tobisu, Mamoru
    Chatani, Naoto
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2017, 90 (03) : 332 - 342
  • [26] Iridium-catalyzed C-H borylation of benzylic amines: Reaction development and substrate scope
    Hale, Lillian V. A.
    Ringgold, Marissa A.
    Roering, Andrew J.
    Squier, Philip A.
    Capaldi, Jessica M.
    Butler, Emily R.
    Clark, Timothy B.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [27] Photocarboxylation of Benzylic C-H Bonds
    Meng, Qing-Yuan
    Schirmer, Tobias E.
    Berger, Anna Lucia
    Donabauer, Karsten
    Koenig, Burkhard
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) : 11393 - 11397
  • [28] Direct Borylation of Primary C-H Bonds in Functionalized Molecules by Palladium Catalysis
    Zhang, Li-Sheng
    Chen, Guihua
    Wang, Xin
    Guo, Qing-Yun
    Zhang, Xi-Sha
    Pan, Fei
    Chen, Kang
    Shi, Zhang-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) : 3899 - 3903
  • [29] A Chemoenzymatic Cascade for the Formal Enantioselective Hydroxylation and Amination of Benzylic C-H Bonds
    Zhang, Yuqing
    Huang, Chen
    Kong, Weixi
    Zhou, Liya
    Gao, Jing
    Hollmann, Frank
    Liu, Yunting
    Jiang, Yanjun
    ACS Catalysis, 2024, 14 (23) : 17405 - 17412
  • [30] Catalytic Enantioselective Functionalizations of C-H Bonds by Chiral Iridium Complexes
    Wozniak, Lukasz
    Tan, Jin-Fay
    Qui-Hien Nguyen
    du Vigne, Adrien Madron
    Smal, Vitalii
    Cao, Yi-Xuan
    Cramer, Nicolai
    CHEMICAL REVIEWS, 2020, 120 (18) : 10516 - 10543