Copper-Catalyzed Claisen Rearrangement with AIBN and Allylic Alcohols.

A novel and succinct method for the synthesis of N-cyanomethyl amides from allylic alcohols with AIBN as the nitrile source is developed. Owing to the coordination effect with the copper catalyst, a ketenimine intermediate is formed via couplings of isobutyronitrile radicals. The copper-activated ketenimine could subsequently be intercepted by allylic alcohols and undergo Claisen rearrangement to furnish N-cyanomethyl amides. Further functional group transformations of the N-cyanomethyl amide products are also described.

Citation

Xuyang Yan, Bangkui Yu, Haocheng Zhang, Hanmin Huang. Copper-Catalyzed Claisen Rearrangement with AIBN and Allylic Alcohols. The Journal of organic chemistry. 2022 Dec 16;87(24):16918-16927

PMID: 36449028

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