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Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids.
- Source :
-
Organic letters [Org Lett] 2016 Dec 16; Vol. 18 (24), pp. 6308-6311. Date of Electronic Publication: 2016 Dec 01. - Publication Year :
- 2016
-
Abstract
- A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc) <subscript>2</subscript> and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 18
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 27978696
- Full Text :
- https://doi.org/10.1021/acs.orglett.6b03176