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Defluoroalkylation of sp(3) C-F bonds of industrially relevant hydrofluoroolefins

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Title: Defluoroalkylation of sp(3) C-F bonds of industrially relevant hydrofluoroolefins
Authors: Phillips, NA
Coates, GJ
White, AJP
Crimmin, MR
Item Type: Journal Article
Abstract: A simple, one‐pot procedure is reported for the selective defluoroalkylation of trifluoromethyl alkene derivatives with aldehydes and ketones. The reaction sequence allows construction of a new C−C bond in a highly selective manner from a single sp3 C−F bond of a CF3 group in the presence of sp2 C−F bonds. The scope incorporates industrially relevant fluorocarbons including HFO‐1234yf and HFO‐1234ze. No catalyst, additives or transition metals are required, rather the methodology relies on a recently developed boron reagent. Remarkably, the boron site of this reagent plays a dual role in the reaction sequence, being nucleophilic at boron in the C−F cleavage step (SN2’) but electrophilic at boron en route to the carbon–carbon bond‐forming step (SE2’). The duplicitous behaviour is underpinned by a hydrogen atom migration from boron to the carbon atom of a carbene ligand.
Issue Date: 24-Apr-2020
Date of Acceptance: 1-Feb-2020
URI: http://hdl.handle.net/10044/1/77880
DOI: 10.1002/chem.202000636
ISSN: 0947-6539
Publisher: Wiley
Start Page: 5365
End Page: 5368
Journal / Book Title: Chemistry: A European Journal
Volume: 26
Issue: 24
Copyright Statement: © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: [Phillips, N.A., Coates, G.J., White, A.J.P. and Crimmin, M.R. (2020), Defluoroalkylation of sp3 C−F Bonds of Industrially Relevant Hydrofluoroolefins. Chem. Eur. J.. doi:10.1002/chem.202000636], which has been published in final form at https://doi.org/10.1002/chem.202000636
Sponsor/Funder: Commission of the European Communities
Funder's Grant Number: 677367
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
C-F functionalisation
defluoroalkylation
fluorine
HFOs
trifluoromethyl
TRIFLUOROMETHYL ALKENES
DEFLUOROSILYLATION
BORYL
C−F functionalisation
HFOs
defluoroalkylation
fluorine
trifluoromethyl
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
C-F functionalisation
defluoroalkylation
fluorine
HFOs
trifluoromethyl
TRIFLUOROMETHYL ALKENES
DEFLUOROSILYLATION
BORYL
General Chemistry
03 Chemical Sciences
Publication Status: Published
Online Publication Date: 2020-02-10
Appears in Collections:Chemistry
Grantham Institute for Climate Change
Faculty of Natural Sciences