Citation
N. Yonezawa et al., Specific and chemoselective multi-alpha-arylation reaction of benzoylformic acid with or without decarbonylation in P2O5-MsOH and related acidic media, J ORG CHEM, 65(4), 2000, pp. 941-944
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263
→ ACNP
Volume
65
Issue
4
Year of publication
2000
Pages
941 - 944
Database
ISI
SICI code
0022-3263(20000225)65:4<941:SACMRO>2.0.ZU;2-C
Abstract
In P2O5-MsOH, or related acidic media, benzoylformic acid (1) undergoes thr
ee types of di- or mono-alpha-arylation reactions with or without decarbony
lation ((1) decarbonylative alpha,alpha-diarylation, yielding triarylmethan
ols 6, (2) decarbonylative cl-monoarylation, giving benzophenone derivative
s 7, and (3) alpha,alpha-diarylation without decarbonylation, affording dia
rylated carboxylic acids 5) and one simple decarbonylation, without arylati
on, to form benzoic acid (8), instead of the conventional Friedel-Crafts ac
ylation type reaction. The product ratios are governed by the capability of
the acidic medium to form mixed anhydrides with carboxylic acids and the a
bility of the arenes to accept electrophiles.