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Updated: Aug 9, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium-Catalyzed Allylic C-H Functionalization of Unactivated Alkenes with α-Diazocarbonyl Compounds
Pinki Sihag1, Trisha Chakraborty1, Masilamani Jeganmohan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India.
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.
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