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

被引:2
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 44 条
  • [31] 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
    [J]. SCIENCE, 2018, 359 (6377) : 759 - +
  • [32] From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions
    Shao, Qian
    Wu, Kevin
    Zhuang, Zhe
    Qian, Shaoqun
    Yu, Jin-Quan
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) : 833 - 851
  • [33] Ruthenium-Catalyzed Oxidative Annulation of Anilines using Benzothiazole as a Removable Directing Group
    Sharma, Shivani
    Singh, Sukanya
    Kumari, Akhilesh
    Sawant, Devesh M.
    Pardasani, Ram T.
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) : 728 - 736
  • [34] Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds
    Su, Bo
    Hartwig, John F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (09)
  • [35] Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct C-C Bonds (Nobel Lecture)
    Suzuki, Akira
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) : 6722 - 6737
  • [36] Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp3)-H Amidation
    Tong, Hua-Rong
    Zheng, Wenrui
    Lv, Xiaoyan
    He, Gang
    Liu, Peng
    Chen, Gong
    [J]. ACS CATALYSIS, 2020, 10 (01): : 114 - 120
  • [37] Direct Amination of Benzylic Pinacol Boronates by an Aminoazanium
    Xu, Jianeng
    Qin, Yucheng
    Liu, Chao
    [J]. SYNLETT, 2023, 34 (18) : 2244 - 2248
  • [38] Palladium-Catalyzed Asymmetric Arylation of C(sp3)-H Bonds of Aliphatic Amides: Controlling Enantioselectivity Using Chiral Phosphoric Amides/Acids
    Yan, Shao-Bai
    Zhang, Song
    Duan, Wei-Liang
    [J]. ORGANIC LETTERS, 2015, 17 (10) : 2458 - 2461
  • [39] Palladium(II)-Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp3)-H Bonds Enabled by a 2-Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids
    Yan, Sheng-Yi
    Han, Ye-Qiang
    Yao, Qi-Jun
    Nie, Xing-Liang
    Liu, Lei
    Shi, Bing-Feng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (29) : 9093 - 9097
  • [40] Boronic acid compounds as potential pharmaceutical agents
    Yang, WQ
    Gao, XM
    Wang, BH
    [J]. MEDICINAL RESEARCH REVIEWS, 2003, 23 (03) : 346 - 368