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Adamantane March 6 ChemRxiv.pdf (841.51 kB)

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

revised on 07.03.2019, 00:33 and posted on 07.03.2019, 14:44 by Hai-Bin Yang, Abigail Feceu, David Martin

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.


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UC Riverside


United States

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