Pseudo-4-Component Photoredox-catalyzed Alkylative Amidination / Carbamoylation of Styrenes with Isocyanides and Redox-Active Esters

11 February 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report a photoredox-catalyzed pseudo-four-component process for the alkylative amidination of styrenes using isocya-nides and redox-active esters (RAEs). This redox-neutral radical-polar crossover reaction shows broad functional group tol-erance. The RAE serves as both a radical and nucleophile source, with the initially released phthalimide anion reintegrated into the final product. The resulting amidines can be readily derivatized into amides, tetrazoles, nitriles, or aldehydes, en-hancing the synthetic utility of this approach.

Keywords

Photoredox catalysis
Multicomponent reaction
difunctionalization of alkenes
Redox-active esters
isocyanides

Supplementary materials

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Electronic Supplementary Information
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Experimental details, Ppocedures, characterization data, and NMR spectra.
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