Imperial College London
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Professor Mark R. Crimmin

Faculty of Natural Sciences, Department of Chemistry

Professor of Organometallic Chemistry
 
 
 
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Contact

 

+44 (0)20 7594 2846m.crimmin Website

 
 
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Location

 

501NMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Phillips:2020:10.1002/chem.202000636,
author = {Phillips, NA and Coates, GJ and White, AJP and Crimmin, MR},
doi = {10.1002/chem.202000636},
journal = {Chemistry: A European Journal},
pages = {5365--5368},
title = {Defluoroalkylation of sp(3) C-F bonds of industrially relevant hydrofluoroolefins},
url = {http://dx.doi.org/10.1002/chem.202000636},
volume = {26},
year = {2020}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - A simple, onepot 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 HFO1234yf and HFO1234ze. 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 bondforming step (SE2’). The duplicitous behaviour is underpinned by a hydrogen atom migration from boron to the carbon atom of a carbene ligand.
AU  - Phillips,NA
AU  - Coates,GJ
AU  - White,AJP
AU  - Crimmin,MR
DO  - 10.1002/chem.202000636
EP  - 5368
PY  - 2020///
SN  - 0947-6539
SP  - 5365
TI  - Defluoroalkylation of sp(3) C-F bonds of industrially relevant hydrofluoroolefins
T2  - Chemistry: A European Journal
UR  - http://dx.doi.org/10.1002/chem.202000636
UR  - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000521382800001&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
UR  - https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202000636
UR  - http://hdl.handle.net/10044/1/77880
VL  - 26
ER  -
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