Issue 12, 2024

Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition

Abstract

We herein report a base-controlled α- or γ-difluoroallylation of alkylidene malonates with trifluoromethyl alkenes, providing various gem-difluoro-1,5-dienes with excellent regioselectivity. Upon irradiation with visible light in the presence of fac-Ir(ppy)3, the intramolecular crossed [2 + 2] photocycloaddition of gem-difluoro-1,5-dienes leads to the formation of highly substituted bicyclo[2.1.1]hexanes in good to excellent yields via an energy transfer pathway.

Graphical abstract: Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition

Supplementary files

Article information

Article type
Research Article
Submitted
29 Mar 2024
Accepted
28 Apr 2024
First published
30 Apr 2024

Org. Chem. Front., 2024,11, 3421-3426

Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition

W. Zeng, M. Li, S. Wu, A. Abdukade and L. Zhou, Org. Chem. Front., 2024, 11, 3421 DOI: 10.1039/D4QO00559G

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