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Defluorosilylation of industrially relevant fluoroolefins using nucleophilic silicon reagents

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Title: Defluorosilylation of industrially relevant fluoroolefins using nucleophilic silicon reagents
Authors: Crimmin, MR
Coates, G
Tan, HY
Kalff, C
White, A
Item Type: Journal Article
Abstract: 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 sp2 or sp3 C-F bonds into C-Si bonds by two modes of nucleophilic attack (SNV or SN2'). 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 catalysed defluorosilylation routes.
Issue Date: 27-Jun-2019
Date of Acceptance: 27-Jun-2019
URI: http://hdl.handle.net/10044/1/71022
DOI: https://dx.doi.org/10.1002/anie.201906825
ISSN: 1433-7851
Journal / Book Title: Angewandte Chemie - International Edition
Copyright Statement: © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the article, which has been published in final form at https://doi.org/10.1002/anie.201906825
Sponsor/Funder: Commission of the European Communities
Funder's Grant Number: 677367
Keywords: C-F Bond Activation
HFO-1234yf
HFO-1234ze
fluorine
silicon
C-F Bond Activation
HFO-1234yf
HFO-1234ze
fluorine
silicon
03 Chemical Sciences
Organic Chemistry
Publication Status: Published online
Conference Place: Germany
Embargo Date: 2020-06-27
Online Publication Date: 2019-06-27
Appears in Collections:Chemistry



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