Palladium-catalyzed reaction of 2-hydroxy-2-methylpropiophenone with aryl bromides: a unique multiple arylation via successive C-C and C-H bond cleavages

Hiroyuki Wakui; Satoshi Kawasaki; Tetsuya Satoh; Masahiro Miura; Masakatsu Nomura

doi:10.1021/ja0477874

Palladium-catalyzed reaction of 2-hydroxy-2-methylpropiophenone with aryl bromides: a unique multiple arylation via successive C-C and C-H bond cleavages

J Am Chem Soc. 2004 Jul 21;126(28):8658-9. doi: 10.1021/ja0477874.

Authors

Hiroyuki Wakui¹, Satoshi Kawasaki, Tetsuya Satoh, Masahiro Miura, Masakatsu Nomura

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 15250711
DOI: 10.1021/ja0477874

Abstract

2-Hydroxy-2-methylpropiophenone undergoes a unique multiple arylation via C-C and C-H bond cleavages upon treatment with excess aryl bromides in the presence of a palladium catalyst to give 1,1,2,2-tetraarylethanes and 4,4-diaryl-1-phenylisochroman-3-ones.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Carbon / chemistry*
Catalysis
Hydrocarbons, Brominated / chemistry*
Hydrogen Bonding
Molecular Structure
Palladium / chemistry*
Propiophenones / chemical synthesis
Propiophenones / chemistry*

Substances

Hydrocarbons, Brominated
Propiophenones
Palladium
Carbon
2-hydroxy-2-methylpropiophenone