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Highly Regioselective Sequential 1,1‐Dihydrosilylation of Terminal Aliphatic Alkynes with Primary Silanes
Author(s) -
Cheng Zhaoyang,
Xing Shipei,
Guo Jun,
Cheng Biao,
Hu LanFang,
Zhang XingHong,
Lu Zhan
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900079
Subject(s) - regioselectivity , chemistry , silanes , hydrosilylation , alkyne , catalysis , combinatorial chemistry , derivative (finance) , double bond , markovnikov's rule , silicon , organic chemistry , silane , financial economics , economics
Summary of main observation and conclusion A regioselective double 1,1‐hydrosilylation of terminal aliphatic alkynes with primary silanes catalyzed by one cobalt catalyst has been developed. gem ‐Bis(dihydrosilyl)alkanes containing four silicon‐hydrogen bonds are efficiently constructed in an atom‐economical manner. Tolerated substrates include simplest alkyne‐ethyne, a complicated drug derivative and various functionalized terminal aliphatic alkynes. Asymmetric approach using two catalysts is achieved with excellent enantioselectivities to access corresponding chiral products. The transformations of Si—H bonds into Si—C, Si—O, and Si—F bonds and the synthesis of enantioriched α ‐hydroxysilane show synthetic utility.