Selective Reduction of Carboxylic Acids to Aldehydes Catalyzed by B(C6F5)3

被引：86
|
作者：
Bezier, David [1 ]
Park, Sehoon [1 ]
Brookhart, Maurice [1 ]
机构：
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 03期
基金：
美国国家科学基金会;
关键词：
ONE-POT CONVERSION; CHEMOSELECTIVE CONVERSION; ORGANIC-COMPOUNDS; METHYL SULFIDE; HYDROGENATION; CHLORIDE; HYDRIDE; KETONES; HYDROSILATION;
D O I：
10.1021/ol303296a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
B(C6F5)(3) efficiently catalyzes hydrosilylation of aliphatic and aromatic carboxylic acids to produce disilyl acetals under mild conditions. Catalyst loadings can be as low as 0.05 mol %, and bulky tertiary silanes are favored to give selectively the acetals. Acidic workup of the disilyl acetals results in the formation of aldehydes in good to excellent yields.
引用
收藏
页码：496 / 499
页数：4
相关论文
共 50 条
  • [41] B(C6F5)3-Catalyzed Reductive Denitrogenation of Benzonitrile Derivatives
    Peng, Yi
    Oestreich, Martin
    ORGANIC LETTERS, 2022, 24 (15) : 2940 - 2943
  • [42] B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols
    Zhou, Jiaming
    Huang, Jin
    Lu, Changhui
    Jiang, Huanfeng
    Huang, Liangbin
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (16) : 3962 - 3967
  • [43] B(C6F5)3-Catalyzed (Convergent) Disproportionation Reaction of lndoles
    Han, Yuxi
    Zhang, Sutao
    He, Jianghua
    Zhang, Yuetao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) : 7399 - 7407
  • [44] B(C6F5)3-Catalyzed Synthesis of Benzofused-Siloles
    Curless, Liam D.
    Ingleson, Michael J.
    ORGANOMETALLICS, 2014, 33 (24) : 7241 - 7246
  • [45] B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes
    Schwier, T
    Rubin, M
    Gevorgyan, V
    ORGANIC LETTERS, 2004, 6 (12) : 1999 - 2001
  • [46] B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
    Zhang, Yangyang
    Zhang, Xinzhi
    Zhao, Jincheng
    Jiang, Jun
    Organic and Biomolecular Chemistry, 2021, 19 (26): : 5772 - 5776
  • [47] B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
    Zhang, Yangyang
    Zhang, Xinzhi
    Zhao, Jincheng
    Jiang, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (26) : 5772 - 5776
  • [48] (C6F5)3B Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with α-Aryl α-Diazoesters
    Yu, Zhunzhun
    Li, Yongfeng
    Shi, Jiameng
    Ma, Ben
    Liu, Lu
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) : 14807 - 14811
  • [49] Catalytic reduction of ketones and aldehydes with Et2O/B(C6F5)3 frustrated Lewis pairs
    Ginovska-Pangovska, Bojana
    Hackel, Arielle
    Camaioni, Donald
    Schenter, Gregory
    Kathmann, Shawn
    Autrey, Tom
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [50] A novel B(C6F5)3-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes
    Gevorgyan, V
    Rubin, M
    Benson, S
    Liu, JX
    Yamamoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 6179 - 6186
12345