Acid-mediated specific alpha,alpha-diarylation and alpha-monoarylation reactions of pyruvic acid with/without decarbonylation

Authors
Yonezawa, N Hino, T Kinuno, T Matsuki, T Ikeda, T
Citation
N. Yonezawa et al., Acid-mediated specific alpha,alpha-diarylation and alpha-monoarylation reactions of pyruvic acid with/without decarbonylation, SYN COMMUN, 29(10), 1999, pp. 1687-1695
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
10
Year of publication
1999
Pages
1687 - 1695
Database
ISI
SICI code
0039-7911(1999)29:10<1687:ASAAAR>2.0.ZU;2-O
Abstract
Pyruvic acid (3) was found to be arylated chemoselectively at the alpha-ket ocarbonyl carbon in P2O5-MsOH affording decarbonylative alpha,alpha-diaryla ted products 5, decarbonylative alpha-monoarylated compounds 6, or non-deca rbonylative alpha,alpha-diarylated adducts 7 depending on the reactivity of arenes (4a-g), in contrast to Lewis acid-catalyzed reaction of its acid ch loride (2).