Catalysis

Catalyst-Controlled C–H Functionalization of Adamantanes using Selective H-Atom Transfer

David Martin UC Riverside

Abstract

A new method for the direct functionalization of diamondoids has been developed using photoredox and H-atom transfer catalysis. This C–H alkylation reaction has excellent chemoselectivity for the strong 3º C–H bonds of adamantanes in polyfunctional molecules. In substrate competition reactions, a reversal in selectivity is observed for the new H-atom transfer catalyst reported here when compared to six known photochemical systems. Derivatization of a broad scope of diamondoids and adamantane-containing drugs highlights the versatility and functional group tolerance of this C–H functionalization strategy.

Content

Thumbnail image of Adamantane March 6 ChemRxiv.pdf
download asset Adamantane March 6 ChemRxiv.pdf 0.82 MB [opens in a new tab]