Rhodium-Catalyzed Allylic C–H Functionalization of Unactivated Alkenes with α-Diazocarbonyl Compounds
Pinki Sihag, Trisha Chakraborty, Masilamani Jeganmohan
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.
Topics & Concepts
ChemistryCyclopropanationDiazoAllylic rearrangementAlkeneCatalysisRhodiumAcceptorFunctional groupCombinatorial chemistryTsuji–Trost reactionOrganic chemistryPhysicsPolymerCondensed matter physicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions