Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

Takuma Yagyu; Yusuke Takemoto; Akira Yoshimura; Viktor V Zhdankin; Akio Saito

doi:10.1021/acs.orglett.7b00742

Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

Org Lett. 2017 May 19;19(10):2506-2509. doi: 10.1021/acs.orglett.7b00742. Epub 2017 May 4.

Authors

Takuma Yagyu¹, Yusuke Takemoto¹, Akira Yoshimura², Viktor V Zhdankin², Akio Saito¹

Affiliations

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan , and.
² Department of Chemistry and Biochemistry, University of Minnesota , Duluth, Minnesota 55812 United States.

PMID: 28471179
DOI: 10.1021/acs.orglett.7b00742

Abstract

The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf₂NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.