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Remote Hydroxylation through Radical Translocation and Polar Crossover.
- Source :
-
Angewandte Chemie . Jun2015, Vol. 127 Issue 27, p7948-7952. 5p. - Publication Year :
- 2015
-
Abstract
- Mild conditions are reported for the hydroxylation of aliphatic CH bonds through radical translocation, oxidation to carbocation, and nucleophilic trapping with H2O. This remote functionalization employs fac-[Ir(ppy)3] together with Tz o sulfonate esters and sulfonamides to facilitate the site-selective replacement of relatively inert CH bonds with the more synthetically useful COH group. The hydroxylation of a range of substrates and the methoxylation of two substrates through 1,6- and 1,7-hydrogen-atom transfer are demonstrated. In addition, a synthesis of the antidepressant fluoxetine using remote hydroxylation as a key step is presented. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 127
- Issue :
- 27
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 103383266
- Full Text :
- https://doi.org/10.1002/ange.201500880