Abstract: C-H and C-C bonds are the most abundant bonds in majority of organic compounds. Selective functionalization of C-C and C-H bonds would lead to efficient synthesis of complex target molecules, but these transformations are generally of significant challenges. In the past, we have been focusing on a "cut and sew" strategy to synthesize bridged and fused rings by utilizing metal-catalyzed C-C bond activation of four-membered ring ketones. Driven by an objective to develop a “cut and sew” reaction with five-membered ring ketones, we obtained an unexpected discovery and later developed a regioselective ketone α-alkylation reaction using simple olefins. This reaction shows a broad substrate scope and high functional group tolerance, which can be further extended to the intramolecular transformation, a formal Conia-Ene reaction, as well as intermolecular alkenylation with alkynes. Meanwhile, driven by the need to improve the efficiency of the ketone alkylation reaction, we accidentally discovered an approach for catalytic C-C bond activation of cyclopentanones and some cyclohexanones, in which the proximal α C-C bond was cleaved and subsequently coupled with a β-aryl group through C-H activation. More recently, activation of the distal C-C bond in these unstrained ketones was enabled through using a bulkier catalyst system.

<b>Award Address </b>(Arthur C. Cope Early Career Scholars Award sponsored by Arthur C. Cope Fund). C–C and C–H functionalization of ketones

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Award Address (Arthur C. Cope Early Career Scholars Award sponsored by Arthur C. Cope Fund). C–C and C–H functionalization of ketones