This Letter describes the development of a method for the Pd-catalyzed electrochemical acetoxylation of C–H bonds. The oxidation step of the catalytic cycle is probed through cyclic voltammetry and bulk electrolysis studies of a pre-formed palladacycle of 8-methylquinoline. A catalytic system for C–H acetoxylation is then developed and optimized with respect to the cell configuration, rate of oxidation, and chemistry at the counter electrode. This transformation is then applied to substrates containing various directing groups and to the acetoxylation of both C(sp2)–H and C(sp3)–H bonds.

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A Solvent-Free Amidation of Vinylogous Esters via Direct Aziridination. -A microwave-mediated aziridination of α,β-unsaturated ketones and esters through the decomposition of ethyl azidoformate is developed. When this reaction is applied to cyclic vinylogous esters like (VIII) or (X), N-functionalization at the α-position occurs. Based on NMR analysis, these amidation products appear to be formed from the desired aziridine. -(MCLAUGHLIN*, E. C.; SHRESTHA, A.; FLETCHER, M. H.; STEINAUER, N. S.; SHINN, M. K.; SHAHID, S. M.; Tetrahedron Lett. 54 (2013) 40, 5461-5463, http://dx.