Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation

Exploiting charge-transfer complexes in visible light-promoted single-electron redox reactions is a promising route for opening novel synthetic pathways, and catalytic approaches to complex formation are critical for facilitating this chemistry. This report describes the use of a substituted hydroqu...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (1), p.446-450
Main Authors: Tasnim, Tarannum, Ryan, Calvin, Christensen, Miranda L, Fennell, Christopher J, Pitre, Spencer P
Format: Article
Language:English
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Summary:Exploiting charge-transfer complexes in visible light-promoted single-electron redox reactions is a promising route for opening novel synthetic pathways, and catalytic approaches to complex formation are critical for facilitating this chemistry. This report describes the use of a substituted hydroquinone catalyst to promote radical perfluoroalkylation reactions. Mechanistic studies indicate that the reaction is initiated through formation of a visible light-absorbing halogen bonding complex between the hydroquinone catalyst and the perfluoroalkyl halide radical precursor.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04139