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Environmentally Benign and User-Friendly Generation of Nitrile Imines from Hydrazones for 1,3-Dipolar Cycloaddition. | LitMetric

Environmentally Benign and User-Friendly Generation of Nitrile Imines from Hydrazones for 1,3-Dipolar Cycloaddition.

J Org Chem

Guangdong Key Laboratory of Animal Conservation and Resource Utilization, Guangdong Public Laboratory of Wild Animal Conservation and Utilization, Institute of Zoology, Guangdong Academy of Sciences, Guangzhou 510275, Guangdong, China.

Published: August 2022

Nitrile imines are highly reactive and versatile dipoles and conventionally generated from unstable hydrazonyl halides under basic conditions. Herein, we report the first green and user-friendly protocol for generation of nitrile imines from Oxone-KBr oxidation of hydrazones and base-promoted dehydrobromination. The nitrile imines were demonstrated for 1,3-dipolar cycloaddition with various dipolarophiles, including alkene and alkyne groups. With its green nature, ease of operation, and air and moisture tolerance, we expect our method will find wide applications in organic synthesis.

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Source
http://dx.doi.org/10.1021/acs.joc.2c01391DOI Listing

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