Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled using DMSO as the solvent

Author:

Weisheitelová Ivana1ORCID,Varma Naisargi2ORCID,Chudoba Josef3,Burdziński Gotard4,Sikorski Marek2ORCID,Cibulka Radek1ORCID

Affiliation:

1. Department of Organic Chemistry, University of Chemistry and Technology, Prague, 16628 Prague, Czech Republic

2. Faculty of Chemistry, Adam Mickiewicz University, 61-614 Poznań, Poland

3. Central Laboratories, University of Chemistry and Technology, Prague, 16628 Prague, Czech Republic

4. Faculty of Physics, Adam Mickiewicz University, 61-614 Poznań, Poland

Abstract

Irradiation of a solution of an unsaturated benzyl alcohol in DMSO under oxygen leads to ketone formation. Side-oxidations are minimized, thanks to the protective role of the DMSO solvent against singlet oxygen. No catalyst or additives are required.

Funder

Grantová Agentura České Republiky

Narodowe Centrum Nauki

Publisher

Royal Society of Chemistry (RSC)

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