Issue 4, 2019

Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

Abstract

We describe a nickel-catalyzed highly regio- and stereoselective migratory fluoro-alkenylation of unactivated alkyl bromides. A unique catalytic cycle merging alkyl nickel chain-walking and defluorinative coupling enables the introduction of a broad array of fluoroalkenyl moieties into carbon chains. Control experiments with other halogenated alkenes demonstrated the essential role of fluorine atoms in this reaction. Notably, the reaction proceeds under mild conditions and allows for the synthesis of a variety of valuable monofluoroalkenes.

Graphical abstract: Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

Supplementary files

Article information

Article type
Edge Article
Submitted
19 Sep 2018
Accepted
08 Nov 2018
First published
09 Nov 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 1144-1149

Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes

L. Zhou, C. Zhu, P. Bi and C. Feng, Chem. Sci., 2019, 10, 1144 DOI: 10.1039/C8SC04162H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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