Rhodium-Catalyzed Remote C(sp3)-H Borylation of Silyl Enol Ethers

被引：41
|
作者：
Li, Jie [1 ]
Qu, Shuanglin [1 ]
Zhao, Wanxiang [1 ]
机构：
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 06期
基金：
中国国家自然科学基金;
关键词：
borylation; C-H activation; isomerization; regioselectivity; rhodium; ALKENE ISOMERIZATION-HYDROBORATION; H BOND ACTIVATION; C-H; ENANTIOSELECTIVE ISOMERIZATION; BIFUNCTIONAL CATALYST; ALLYLIC ALCOHOLS; HECK ARYLATIONS; BORONIC ESTERS; CHAIN-WALKING; FUNCTIONALIZATION;
D O I：
10.1002/anie.201913281
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A rhodium-catalyzed remote C(sp(3))-H borylation of silyl enol ethers (SEEs, E/Z mixtures) by alkene isomerization and hydroboration is reported. The reaction exhibits mild reaction conditions and excellent functional-group tolerance. This method is compatible with an array of SEEs, including linear and branched SEEs derived from aldehydes and ketones, and provides direct access to a broad range of structurally diverse 1,n-borylethers in excellent regioselectivities and good yields. These compounds are precursors to various valuable chemicals, such as 1,n-diols and aminoalcohols.
引用
收藏
页码：2360 / 2364
页数：5
相关论文
共 50 条
  • [1] Rhodium-Catalyzed Remote Borylation of Alkynes and Vinylboronates
    Zhang, Minghao
    Liu, Zheming
    Zhao, Wanxiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (05)
  • [2] Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
    Li, Jie
    Zhao, Pei
    Li, Ruoling
    Yang, Wen
    Zhao, Wanxiang
    ORGANIC LETTERS, 2021, 23 (24) : 9580 - 9585
  • [3] Rhodium-catalyzed α-fluoroalkylation reaction of ketones using silyl enol ethers
    Sato, Kazuyuki
    Higashinagata, Makoto
    Yuki, Takashi
    Tarui, Atsushi
    Omote, Masaaki
    Kumadaki, Itsumaro
    Ando, Akira
    JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (01) : 51 - 55
  • [4] Rhodium-Catalyzed Dehydrogenative Silylation of Acetophenone Derivatives: Formation of Silyl Enol Ethers versus Silyl Ethers
    Garces, Karin
    Lalrempuia, Ralte
    Polo, Victor
    Fernandez-Alvarez, Francisco J.
    Garcia-Orduna, Pilar
    Lahoz, Fernando J.
    Perez-Torrente, Jesus J.
    Oro, Luis A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) : 14717 - 14729
  • [5] α-Arylation of Silyl Enol Ethers via Rhodium(III)-Catalyzed C-H Functionalization
    Kou, Xuezhen
    Kou, Kevin G. M.
    ACS CATALYSIS, 2020, 10 (05) : 3103 - 3109
  • [6] Rhodium-Catalyzed PIII-Directed ortho-C-H Borylation of Arylphosphines
    Wen, Jian
    Wang, Dingyi
    Qian, Jiasheng
    Wang, Di
    Zhu, Chendan
    Zhao, Yue
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 2078 - 2082
  • [7] Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation
    He, Jian
    Shao, Qian
    Wu, Qingfeng
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (09) : 3344 - 3347
  • [8] Rhodium-Catalyzed C(sp3)-H Arylation of 8-Methylquinolines with Arylsilanes
    Li, Lin
    Liu, Haidong
    Qian, Yupeng
    Shen, Guohong
    Shi, Yun
    Du, Jiajie
    Luo, Haiqing
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (21) : 2627 - 2632
  • [9] Zn-mediated rhodium-catalyzed α-trifluoromethylation of ketones via silyl enol ethers
    Sato, Kazuyuki
    Yuki, Takashi
    Tarui, Atsushi
    Omote, Masaaki
    Kumadaki, Itsumaro
    Ando, Akira
    TETRAHEDRON LETTERS, 2008, 49 (22) : 3558 - 3561
  • [10] Rhodium-catalyzed intermolecular C(sp3)-H amination in a purely aqueous system
    Lu, Xunbo
    Shi, Yufeng
    Zhong, Fangrui
    GREEN CHEMISTRY, 2018, 20 (01) : 113 - 117
12345