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, Advance Article

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, Advance Article , DOI: 10.1039/D4QO00559G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements