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Issue 42, 2020
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An uncommon use of irradiated flavins: Brønsted acid catalysis

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Abstract

We present that thioacetalization of aldehydes can be induced by blue light irradiation in the presence of a catalytic amount of riboflavin tetraacetate (RFTA) under aerobic conditions. Several control experiments have suggested that the reaction is more likely to be catalyzed by acidic species generated in situ upon light irradiation. We have proposed that single electron transfer from a thiol (RSH) to the excited state of RFTA can take place to give a one-electron oxidized thiol (RSH+˙) and the one-electron reduced RFTA (RFTA˙), which can be trapped by molecular oxygen to be stabilized as Brønsted acids including the protonated RFTA˙ (RFTAH˙). Finally, we have demonstrated that such acidic species can be prepared in advance as a solution and used as Brønsted acid catalysts for not only thioacetalization but also Mannich-type reactions.

Graphical abstract: An uncommon use of irradiated flavins: Brønsted acid catalysis

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Supplementary files

Article information


Submitted
16 Mar 2020
Accepted
08 Apr 2020
First published
09 Apr 2020

Chem. Commun., 2020,56, 5661-5664
Article type
Communication

An uncommon use of irradiated flavins: Brønsted acid catalysis

Y. Arakawa, T. Mihara, H. Fujii, K. Minagawa and Y. Imada, Chem. Commun., 2020, 56, 5661
DOI: 10.1039/D0CC01960G

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