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[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes.

Authors :
Zeng TT
Xuan J
Ding W
Wang K
Lu LQ
Xiao WJ
Source :
Organic letters [Org Lett] 2015 Aug 21; Vol. 17 (16), pp. 4070-3. Date of Electronic Publication: 2015 Aug 07.
Publication Year :
2015

Abstract

A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.

Details

Language :
English
ISSN :
1523-7052
Volume :
17
Issue :
16
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
26250789
Full Text :
https://doi.org/10.1021/acs.orglett.5b01994