Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

被引:22
作者
Pandey, Vipin K. [1 ]
Tiwari, Chandra Shekhar [1 ]
Rit, Arnab [1 ]
机构
[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India
关键词
D O I
10.1021/acs.orglett.1c00106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- and solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.
引用
收藏
页码:1681 / 1686
页数:6
相关论文
共 57 条
[1]   Alkyne and Alkene Insertion into Metal-Heteroatom and Metal-Hydrogen Bonds: The Key Stages of Hydrofunctionalization Process [J].
Ananikov, Valentine P. ;
Beletskaya, Irina P. .
HYDROFUNCTIONALIZATION, 2013, 43 :1-19
[2]  
[Anonymous], 1962, Hydroboration
[3]  
[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation
[4]   Dihydroboration of Alkyl Nitriles Catalyzed by an Osmium-Polyhydride: Scope, Kinetics, and Mechanism [J].
Babon, Juan C. ;
Esteruelas, Miguel A. ;
Fernandez, Israel ;
Lopez, Ana M. ;
Onate, Enrique .
ORGANOMETALLICS, 2020, 39 (21) :3864-3872
[5]   Recent Advances in Transition Metal-Catalyzed Hydrogenation of Nitriles [J].
Bagal, Dattatraya B. ;
Bhanage, Bhalchandra M. .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :883-900
[6]   Extremely efficient hydroboration of ketones and aldehydes by copper carbene catalysis [J].
Bagherzadeh, Sharareh ;
Mankad, Neal P. .
CHEMICAL COMMUNICATIONS, 2016, 52 (19) :3844-3846
[7]   Aluminum-Catalyzed Hydroboration of Alkenes [J].
Bismuto, Alessandro ;
Cowley, Michael J. ;
Thomas, Stephen P. .
ACS CATALYSIS, 2018, 8 (03) :2001-2005
[8]   A NEW TECHNIQUE FOR THE CONVERSION OF OLEFINS INTO ORGANOBORANES AND RELATED ALCOHOLS [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (21) :5694-5695
[9]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[10]   Catalytic Hydroboration of Carbonyl Derivatives, Imines, and Carbon Dioxide [J].
Chong, Che Chang ;
Kinjo, Rei .
ACS CATALYSIS, 2015, 5 (06) :3238-3259