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Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols

Author:
Fava, Eleonora, Nakajima, Masaki, Nguyen, Anh L. P., Rueping, Magnus
Source:
Journal of organic chemistry 2016 v.81 no.16 pp. 6959-6964
ISSN:
1520-6904
Subject:
aldehydes, alkenes, alkynes, catalysts, chemical structure, electron transfer, organic chemistry
Abstract:
A visible light photoredox-catalyzed aldehyde olefin cyclization is reported. The method represents a formal hydroacylation of alkenes and alkynes and provides chromanol derivatives in good yields. The protocol takes advantage of the double role played by trialkylamines (NR₃) which act as (i) electron donors for reducing the catalyst and (ii) proton donors to activate the substrate via a proton-coupled electron transfer.
Agid:
5505808