Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines

Abstract

A visible-light-mediated metal-free oxidation of 1-benzyl-3,4-dihydroisoquinolines (1-BnDHIQs) for the switchable preparation of a wide range of 1-benzoylisoquinolines (BzIQs) and 1-benzoyl-3,4-dihydroisoquinolines (BzDHIQs) is realized using dioxygen as the oxidant. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigations suggest that a radical pathway and an ionic pathway may exist simultaneously, with both pathways proceeding via a common key peroxide intermediate to give the oxidized products.

Key words

visible light - 1-benzoylisoquinolines - 1-benzoyl-3,4-dihydroisoquinolines - metal-free - dioxygen

Publication History

Received: 10 July 2023

Accepted after revision: 25 August 2023

Accepted Manuscript online:
25 August 2023

Article published online:
04 October 2023

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