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

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 pi-allyl intermediate has been synthesized and proved to be the active intermediate. Additional mechanistic investigations aided the elucidation of the plausible reaction mechanism.

Automated summary

A redox-neutral mild methodology for allylic C-H alkylation of unactivated alkenes with diazo compounds is demonstrated. The protocol avoids the undesired cyclopropanation of alkenes and is compatible with various functional groups. A rhodacycle pi-allyl intermediate is synthesized and proven to be the active intermediate, with additional mechanistic investigation aiding in elucidating the possible reaction mechanism.