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Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals

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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

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Publication details

The article was received on 24 Nov 2018, accepted on 15 Jan 2019 and first published on 16 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05237A
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C8SC05237A

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