In:
European Journal of Organic Chemistry, Wiley, Vol. 2020, No. 10 ( 2020-03-15), p. 1579-1585
Abstract:
New flavin‐based photocatalytic systems used for chemoselective aerobic visible‐light oxidations have been developed by tuning the flavin structure and reaction conditions. 1,3‐Dimethyl‐7‐trifluoromethylalloxazine ( 2 ) and 10‐butyl‐3‐methyl‐7‐trifluoromethylisoalloxazine ( 3 ) were shown to mediate the selective oxidation of benzyl alcohols to form aldehydes in the presence of Cs 2 CO 3 . Flavin 3 was superior in the oxidation of toluene derivatives to form aldehydes in the presence of trifluoroacetic acid. On the other hand, photooxidations provided by ethylene‐bridged quaternary flavinium salt 1 gave the corresponding carboxylic acids. The usefulness of the developed catalytic systems using 1 – 3 was also demonstrated in the oxidation of secondary benzylic and aliphatic alcohols, and benzylic methylene groups to form the corresponding ketones. The systems have the advantage of a broad substrate scope and metal‐free conditions, which distinguish them from the previously reported flavin photooxidation reactions.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2020.10
DOI:
10.1002/ejoc.201901628
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
1475010-7
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