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

Eleonora Fava | Zendy; Masaki Nakajima | Zendy; Anh L. P. Nguyen | Zendy; Magnus Rueping | Zendy

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

Author(s) -

Eleonora Fava,

Masaki Nakajima,

Anh L. P. Nguyen,

Magnus Rueping

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b01006

Subject(s) - hydroacylation , ketyl , catalysis , photoredox catalysis , olefin fiber , chemistry , substrate (aquarium) , coupling (piping) , proton , photochemistry , umpolung , aldehyde , combinatorial chemistry , organic chemistry , physics , materials science , benzophenone , photocatalysis , quantum mechanics , metallurgy , oceanography , nucleophile , geology

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.

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