Organophotocatalytic [2+2] cycloaddition of electron-deficient styrenes

14 July 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A visible light organophotocatalytic [2+2] cycloaddition of electron-deficient styrenes is described. Photocatalytic [2+2] cycloadditions are typically performed with electron-rich styrene derivatives or α,β-unsaturated alkenes, and with transition-metal-based catalysts. We have discovered that an organic cyanoarene photocatalyst is able to deliver high-value cyclobutane products bearing electron-deficient aryl substituents in good yields. A range of electron-deficient substituents are tolerated and both homodimerizations and intramolecular [2+2] cycloadditions to fused bicyclic systems are available using this methodology.

Keywords

Cycloaddition
Organophotocatalysis
Cyclobutane
Electron-deficient Styrenes
Energy Transfer

Supplementary materials

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Description
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Supporting Information
Description
Synthetic procedures, characterisation data, NMR spectra, and X-Ray data.
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