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Visible-Light-Promoted Activation of Unactivated C(sp 3 )-H Bonds and Their Selective Trifluoromethylthiolation.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2016 Dec 21; Vol. 138 (50), pp. 16200-16203. Date of Electronic Publication: 2016 Dec 09. - Publication Year :
- 2016
-
Abstract
- Selective functionalization of ubiquitous C(sp <superscript>3</superscript> )-H bonds using visible light is a highly challenging yet desirable goal in organic synthesis. The development of such processes relies on both rational design and serendipitous discoveries from innovative tools such as screening technologies. Applying a mechanism-based screening strategy, we herein report photoredox-mediated hydrogen atom transfer catalysis for the selective activation of otherwise unactivated C(sp <superscript>3</superscript> )-H bonds, followed by their trifluoromethylthiolation, which has high potential as a late-stage functionalization tool. The generality of this method is exhibited through incorporation of the trifluoromethylthio group in a large number of C(sp <superscript>3</superscript> )-H bonds with high selectivity without the need for an excess of valuable substrate.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 138
- Issue :
- 50
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 27935270
- Full Text :
- https://doi.org/10.1021/jacs.6b09970