title: Nucleophilic metal complexes as acylation catalysts: solvent-dependent "switch" mechanisms leading to the first catalyzed Staudinger reaction.
abstract: [formula: see text] 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 beta-lactams.
authors.affiliation: Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218, USA.
authors.forename: H
authors.initials: H
authors.lastname: Wack
authors.forename: W J
authors.initials: WJ
authors.lastname: Drury
authors.forename: A E
authors.initials: AE
authors.lastname: Taggi
authors.forename: D
authors.initials: D
authors.lastname: Ferraris
authors.forename: T
authors.initials: T
authors.lastname: Lectka
mesh_terms: D000215:Acylation; D002384:Catalysis; D003035:Cobalt; D007202:Indicators and Reagents; D007769:Lactams / Q000138:chemical synthesis*; D009942:Organometallic Compounds; D012964:Sodium; D012997:Solvents
chemical_list: D007202:Indicators and Reagents; D007769:Lactams; D009942:Organometallic Compounds; D012997:Solvents; D003035:Cobalt; D012964:Sodium