Organic Chemistry

Direct photolysis of 4-tert-alkyl-1,4-dihydropyridines under blue-light irradiation for the generation of tertiary alkyl radicals

Authors

Abstract

Herein, we disclose a direct photolysis approach for the generation of tertiary alkyl radicals from 4-tert-alkyl-1,4-dihydropyridines (DHPs) under blue LED irradiation, as exemplified in a photochemical Giese reaction. Radical generation occurs under mild conditions, does not require the use of exogenous photocatalysts or oxidants, and the Giese reaction is compatible with a range of 4-tert-alkyl-DHPs and Michael acceptors (23 examples, up to 86% yield). Mechanistic investigations reveal that the presence of base is crucial for radical generation.

Version notes

New scope examples and mechanistic studies have been added.

Content

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Supplementary material

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Electronic Supplementary Materials
Contains experimental procedures, compound characterization, UV-vis studies, and NMR spectra.