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B(C 6 F 5 ) 3 /Amine‐Catalyzed C(sp)−H Silylation of Terminal Alkynes with Hydrosilanes: Experimental and Theoretical Studies
Author(s) -
Ma Yuanhong,
Lou ShaoJie,
Luo Gen,
Luo Yong,
Zhan Gu,
Nishiura Masayoshi,
Luo Yi,
Hou Zhaomin
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809533
Subject(s) - dabco , silylation , catalysis , surface modification , chemistry , lewis acids and bases , transition metal , amine gas treating , boron , base (topology) , medicinal chemistry , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics
Transition metal catalyzed C−H functionalization of organic compounds has proved to be a useful atom‐efficient strategy in organic synthesis. In contrast, main‐group‐element‐based catalytic processes for C−H functionalization have remained underexplored to date. Reported herein is the catalytic C(sp)−H silylation of a wide range of terminal alkynes with hydrosilanes by using a combination of B(C 6 F 5 ) 3 and an organic base such as triethylenediamine (DABCO). This protocol constitutes the first example of boron‐catalyzed C(sp)−H functionalization, offering a convenient route for the synthesis of a variety of alkynylsilanes. Experimental and computational studies have revealed that DABCO plays two crucial roles (Lewis base and Brønsted base) in this catalytic transformation.