Journal article
Catalyst-Controlled C–H Functionalization of Adamantanes Using Selective H-Atom Transfer
ACS catalysis, Vol.9(6), pp.5708-5715
06/07/2019
DOI: 10.1021/acscatal.9b01394
Abstract
A 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 3° 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 in comparison to five 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.
Details
- Title: Subtitle
- Catalyst-Controlled C–H Functionalization of Adamantanes Using Selective H-Atom Transfer
- Creators
- Hai-Bin Yang - Department of Chemistry, University of California Riverside, Riverside, California 92521, United StatesAbigail Feceu - Department of Chemistry, University of California Riverside, Riverside, California 92521, United StatesDavid B. C Martin - Department of Chemistry, University of California Riverside, Riverside, California 92521, United States
- Resource Type
- Journal article
- Publication Details
- ACS catalysis, Vol.9(6), pp.5708-5715
- DOI
- 10.1021/acscatal.9b01394
- ISSN
- 2155-5435
- eISSN
- 2155-5435
- Grant note
- DOI: 10.13039/100007602, name: University of California, Riverside
- Language
- English
- Date published
- 06/07/2019
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984065751602771
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