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

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) electr...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-08, Vol.81 (16), p.6959-6964
Main Authors: Fava, Eleonora, Nakajima, Masaki, Nguyen, Anh L. P, Rueping, Magnus
Format: Article
Language:English
Subjects:
aldehydes
alkenes
alkynes
Brief Communication
catalysts
chemical structure
electron transfer
organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b01006