Nucleophilic Metal Complexes as Acylation Catalysts: Solvent-Dependent “Switch” Mechanisms Leading to the First Catalyzed Staudinger Reaction
- 12 November 1999
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (12), 1985-1988
- https://doi.org/10.1021/ol9903234
Abstract
Catalytic acylation using complex transition metal salts MCo(CO)4 is demonstrated. Surprisingly, a solvent-dependent mechanistic “switch” results in a Lewis acid-based acylation mechanism in nonpolar media and a nucleophilic mechanism in polar organic media. These observations lead to the first example of a catalyzed Staudinger reaction to form β-lactams.Keywords
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