Issue 9, 2019

Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals

Abstract

A metal-free and photo-free method for the perfluoroalkylative pyridylation of alkenes has been developed via a combination of computational and experimental studies. Density functional theory calculations and control experiments indicate that the homolysis of Rf−X (X = Br, I) bonds by the 4-cyanopyridine-boryl radicals in situ generated from 4-cyanopyridine and B2pin2 is the key step. Sequential addition of Rf radicals to alkenes and the selective cross-coupling of the resulting alkyl radicals and 4-cyanopyridine-boryl radicals gives alkene difunctionalization products with a quaternary carbon center. This method exhibits a broad substrate scope and good functional group compatibility.

Graphical abstract: Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Nov 2018
Accepted
15 Jan 2019
First published
16 Jan 2019
This article is Open Access

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

Chem. Sci., 2019,10, 2767-2772

Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals

J. Cao, G. Wang, L. Gao, H. Chen, X. Liu, X. Cheng and S. Li, Chem. Sci., 2019, 10, 2767 DOI: 10.1039/C8SC05237A

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