Issue 41, 2023

Photocatalytic redox-neutral selective single C(sp3)–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Abstract

Visible-light-promoted site-selective and direct C–F bond functionalization of polyfluorinated iminosulfides was accomplished with alkenes and water under redox-neutral conditions, affording a diverse array of γ-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. A variety of perfluoroalkyl units, including C2F5, C3F7, C4F9, and C5F11 underwent site-selective defluorofunctionalization. This protocol allows high chemoselectivity control and shows excellent functional group tolerance. Mechanistic studies reveal that the remarkable changes of the electron geometries during the defluorination widen the redox window between the substrates and the products and ensure the chemoselectivity of single C(sp3)–F bond cleavage.

Graphical abstract: Photocatalytic redox-neutral selective single C(sp3)–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

Supplementary files

Article information

Article type
Edge Article
Submitted
21 iyl 2023
Accepted
04 okt 2023
First published
07 okt 2023
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., 2023,14, 11566-11572

Photocatalytic redox-neutral selective single C(sp3)–F bond activation of perfluoroalkyl iminosulfides with alkenes and water

T. Wang, Y. Zong, T. Huang, X. Jin, L. Wu and Q. Liu, Chem. Sci., 2023, 14, 11566 DOI: 10.1039/D3SC03771A

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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