Nucleophilic metal complexes as acylation catalysts: Solvent-dependent "switch" mechanisms leading to the first catalyzed Staudinger reaction

Authors
Wack, H Drury, WJ Taggi, AE Ferraris, D Lectka, T
Citation
H. Wack et al., Nucleophilic metal complexes as acylation catalysts: Solvent-dependent "switch" mechanisms leading to the first catalyzed Staudinger reaction, ORG LETT, 1(12), 1999, pp. 1985-1988
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
12
Year of publication
1999
Pages
1985 - 1988
Database
ISI
SICI code
1523-7060(199912)1:12<1985:NMCAAC>2.0.ZU;2-F
Abstract
[GRAPHICS] Catalytic acylation using complex transition metal salts MCo(CO)(4) is demo nstrated. Surprisingly, a solvent-dependent mechanistic "switch" results in a Lewis acid-based acylation mechanism in nonpolar media and a nucleophili c mechanism in polar organic media, These observations lead to the first ex ample of a catalyzed Staudinger reaction to form beta-lactams.