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Rhodium-Catalyzed Allylic C-H Functionalization of Unactivated Alkenes with α-Diazocarbonyl Compounds.

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A redox-neutral mild methodology for the allylic C-H alkylation of unactivated alkenes with diazo compounds is demonstrated. The developed protocol is able to bypass the possibility of the cyclopropanation of… Click to show full abstract

A redox-neutral mild methodology for the allylic C-H alkylation of unactivated alkenes with diazo compounds is demonstrated. The developed protocol is able to bypass the possibility of the cyclopropanation of an alkene upon its reaction with the acceptor-acceptor diazo compounds. The protocol is highly accomplished due to its compatibility with various unactivated alkenes functionalized with different sensitive functional groups. A rhodacycle π-allyl intermediate has been synthesized and proved to be the active intermediate. Additional mechanistic investigations aided the elucidation of the plausible reaction mechanism.

Keywords: functionalization unactivated; alkenes diazocarbonyl; catalyzed allylic; rhodium catalyzed; allylic functionalization; unactivated alkenes

Journal Title: Organic letters
Year Published: 2023

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