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Dehydroxylative Alkylation of α‐Hydroxy Carboxylic Acid Derivatives via a Spin‐Center Shift.
- Source :
-
Angewandte Chemie International Edition . 6/20/2022, Vol. 61 Issue 25, p1-7. 7p. - Publication Year :
- 2022
-
Abstract
- A strategically distinct dehydroxylative alkylation reaction of α‐hydroxy carboxylic acid derivatives with alkenes is developed. The reaction starts with the attack of a 4‐dimethylaminopyridine (DMAP)‐boryl radical to the carbonyl oxygen atom, followed by a spin‐center shift (SCS) to trigger the C−O bond scission. The resulting α‐carbonyl radicals couple with a wide range of alkenes to furnish various alkylated products. This strategy allows for the efficient conversion of a wide array of α‐hydroxy amides and esters derived from several biomass molecules and natural products to value‐added compounds. Experimental and computational studies verified the reaction mechanism. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 61
- Issue :
- 25
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 157396362
- Full Text :
- https://doi.org/10.1002/anie.202201329