B(C6F5)3-Catalyzed Cascade Reduction of Pyridines

被引：83
|
作者：
Liu, Zhi-Yun [1 ,2 ]
Wen, Zhi-Hui [1 ,2 ]
Wang, Xiao-Chen [1 ,2 ]
机构：
[1] Nankai Univ, State Key Lab, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Coll Chem, 94 Weijin Rd, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Coll Chem, 94 Weijin Rd, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 21期
基金：
中国国家自然科学基金;
关键词：
boron; chemoselectivity; homogeneous catalysis; nitrogen heterocycles; reduction; CATALYZED ASYMMETRIC HYDROGENATION; MULTIPLE STEREOGENIC CENTERS; SILYLATIVE REDUCTION; BOND ACTIVATION; HYDROSILYLATION; BORANE; MECHANISM; HYDROSILATION; HETEROCYCLES; DERIVATIVES;
D O I：
10.1002/anie.201702304
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
B(C6F5)(3) has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.
引用
收藏
页码：5817 / 5820
页数：4
相关论文
共 50 条
  • [1] B(C6F5)3-Catalyzed Hydrosilylation of Vinylcyclopropanes
    Long, Peng-Wei
    He, Tao
    Oestreich, Martin
    ORGANIC LETTERS, 2020, 22 (18) : 7383 - 7386
  • [2] B(C6F5)3-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes
    Porwal, Digvijay
    Oestreich, Martin
    SYNTHESIS-STUTTGART, 2017, 49 (20): : 4698 - 4702
  • [3] B(C6F5)3-catalyzed synthesis of benzylic azides
    Wrigley, Michael S.
    Barker, Timothy J.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (19) : 1771 - 1776
  • [4] B(C6F5)3-Catalyzed Silylation of Unsaturated Hydrocarbons
    Feng Xiangqing
    Du Haifeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (10) : 3544 - 3557
  • [5] B(C6F5)3-catalyzed selective chlorination of hydrosilanes
    Dobrovetsky, Roman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [6] B(C6F5)3-Catalyzed Selective Chlorination of Hydrosilanes
    Chulsky, Karina
    Dobrovetsky, Roman
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (17) : 4744 - 4748
  • [7] B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
    Pan, Yixiao
    Luo, Zhenli
    Han, Jiahong
    Xu, Xin
    Chen, Changjun
    Zhao, Haoqiang
    Xu, Lijin
    Fan, Qinghua
    Xiao, Jianliang
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (10) : 2301 - 2308
  • [8] B(C6F5)3-Catalyzed Reduction of Aromatic and Aliphatic Nitro Groups with Hydrosilanes
    Porwal, Digvijay
    Oestreich, Martin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3307 - 3309
  • [9] B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines
    Shi, Lei
    Bao, Robert Li-Yuan
    Zheng, Limin
    Zhao, Rong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (38) : 6550 - 6556
  • [10] Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins
    Rubin, M
    Schwier, T
    Gevorgyan, V
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06): : 1936 - 1940
12345