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
  • [31] Iron-catalyzed Versatile and Efficient C(sp2)-H Borylation
    Kamitani, Masahiro
    Kusaka, Haruki
    Yuge, Hidetaka
    CHEMISTRY LETTERS, 2019, 48 (08) : 898 - 901
  • [32] 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
  • [33] Iridium-Catalyzed C(sp3)-H Borylation Using Silyl-Bipyridine Pincer Ligands
    Kawazu, Ryohei
    Torigoe, Takeru
    Kuninobu, Yoichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (22)
  • [34] 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
  • [35] Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands
    Jones, Margaret R.
    Fast, Caleb D.
    Schley, Nathan D.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (14) : 6488 - 6492
  • [36] Enantioselective palladium-catalyzed C(sp2)-H carbamoylation
    Dong, Wenfeng
    Xu, Guangqing
    Tang, Wenjun
    TETRAHEDRON, 2019, 75 (24) : 3239 - 3247
  • [37] Electrooxidative iridium-catalyzed sp2 C-H activation-annulation leading to cationic π-extended heteroaromatics
    Yang, Qi-Liang
    Guo, Na-Na
    Liu, Shu-Xian
    Zhang, Bei-Ning
    Zou, Guodong
    Wang, Hai-Xia
    Wang, Dong-Chao
    Guo, Hai-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (17): : 4849 - 4856
  • [38] Mechanism and Origins of Enantioselectivity of Iridium-Catalyzed Intramolecular Silylation of Unactivated C(sp3)-H Bonds
    Zhang, Mei
    Liang, Jiaqi
    Huang, Genping
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 2372 - 2376
  • [39] Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions
    Wang, Hao
    Park, Yoonsu
    Bai, Ziqian
    Chang, Sukbok
    He, Gang
    Chen, Gong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (17) : 7194 - 7201
  • [40] Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives
    Britton, Luke
    Skrodzki, Maciej
    Nichol, Gary S.
    Dominey, Andrew P.
    Docherty, Jamie H.
    Thomas, Stephen P.
    ACS CATALYSIS, 2021, 11 (12) : 6857 - 6864
12345