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Transition‐Metal‐Free Defluorosilylation of Fluoroalkenes with Silylboronates
Author(s) -
Gao Pan,
Wang Guoqiang,
Xi Longlong,
Wang Minyan,
Li Shuhua,
Shi Zhuangzhi
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.201900310
Subject(s) - chemistry , silylation , transition metal , combinatorial chemistry , reactivity (psychology) , catalysis , base (topology) , alkoxy group , ligand (biochemistry) , organic chemistry , medicine , mathematical analysis , biochemistry , alkyl , alternative medicine , mathematics , receptor , pathology
Summary of main observation and conclusion Silylated fluoroalkenes are important synthetic intermediates with complementary reactivity, which play a key role in the construction of natural products, pharmaceuticals, and manmade materials. Converting the normally highly stable fluoroalkenes into silylated fluoroalkenes by selective defluorosilylation is a challenging task. Herein, we report a simple, inexpensive and robust defluorosilylation of a variety of fluoroalkenes with silylboronates in the presence of alkoxy base to directly synthesize various silylated fluoroalkenes. The protocol features mild and safe reaction conditions that avoid a catalyst, a transition metal, a ligand, and high reaction temperature and tolerates a wide scope of fluoroalkene substrates without compromising the efficiency. Density functional theory calculations show that transient silyl anion complex undergoes an S N 2’ or S N V substitution, which is responsible for this base‐mediated defluorosilylation.