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