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

Takuma Yagyu, Yusuke Takemoto, Akira Yoshimura, Viktor V. Zhdankin, Akio Saito

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English (US)
Pages (from-to)	2506-2509
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00742
State	Published - May 19 2017

Bibliographical note

Funding Information:
This work was partially supported by a JSPS Grants-in-Aid for Scientific Research (C) (Grant No. 15K07852) and by the Asahi Glass Foundation. V.V.Z. is also thankful to the National Science Foundation (CHE-1262479).

Publisher Copyright:
© 2017 American Chemical Society.

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

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10.1021/acs.orglett.7b00742

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AU - Zhdankin, Viktor V.

AU - Saito, Akio

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

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