Premium
Visible‐Light‐Driven Aerobic Photooxidation of Aldehydes to Methyl Esters Catalyzed by Riboflavin Tetraacetate
Author(s) -
Mühldorf Bernd,
Wolf Robert
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201601504
Subject(s) - chemistry , protonation , photochemistry , catalysis , flavin group , acetal , photocatalysis , riboflavin , oxygen , electron transfer , visible spectrum , acid catalysis , medicinal chemistry , organic chemistry , enzyme , ion , biochemistry , physics , optoelectronics
Riboflavin tetraacetate (RFT) catalyzes the aerobic esterification of para ‐substituted benzaldehydes to their corresponding methyl esters. The reaction proceeds under visible‐light irradiation in MeOH/MeCN in the presence of a Brønsted acid such as HCl. Electron transfer from the in situ formed dimethyl acetal to the photoexcited triplet flavin appears to be a key mechanistic step. The acid catalyzes the formation of the acetal and increases the reduction potential of RFT by protonation. The photocatalyst is regenerated by reaction with atmospheric oxygen, which serves as the terminal oxidant.