11/2016

In this collaboration between the France (GA Tech) and Musaev (Emory) groups the dirhodium-catalyzed beta-(Csp2)–H functionalization of enol ethers, enamides and enecarbamates with acceptor/acceptor carbenes is reported. The reaction is highly efficient and the products are demonstrated to be versatile intermediates for further synthetic elaboration.

Using a combination of experimentals and computational studies the presumptive addition-elimination reaction mechanism was explored, findings from which were translated into reaction design, affording the first successful example of the beta-C–H functionalization of acyclic enol ethers using the acceptor carbene systems.

This transformation represents a significant expansion in the scope of substrates for carbene C–H insertion chemistry for future exploitation.