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Defluorosilylation of Industrially Relevant Fluoroolefins Using Nucleophilic Silicon Reagents
Author(s) -
Coates Greg,
Tan Hui Yee,
Kalff Carolin,
White Andrew J. P.,
Crimmin Mark R.
Publication year - 2019
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.201906825
Subject(s) - reagent , nucleophile , regioselectivity , silylation , chemistry , lithium (medication) , silicon , nucleophilic substitution , magnesium , substitution reaction , catalysis , transition metal , combinatorial chemistry , organic chemistry , medicine , endocrinology
A number of new magnesium and lithium silyl reagents were prepared and shown to be outstanding nucleophiles in reactions with industrially relevant fluoroolefins. These reactions result in a net transformation of either sp 2 or sp 3 C−F bonds into C−Si bonds by two modes of nucleophilic attack (S N V or S N 2′). The methods are mild, proceeding with high chemo‐ and regioselectivity. Mechanistic pathways are described that lead to new substitution patterns from HFO‐1234yf, HFO‐1234ze, and HFO‐1336mzz, previously inaccessible by transition metal catalyzed difluorosilylation routes.