The methoxycarbonylation of aryl chlorides catalysed by palladium complexes of bis(di-tert-butylphosphinomethyl)benzene
- 25 April 2005
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Dalton Transactions
- No. 10,p. 1826-1830
Abstract
A catalyst system based on palladium-1,2-bis-(di-tert-butylphosphinomethyl)benzene (BDTBPMB) shows good activity for the methoxycarbonylation of strongly activated aryl chlorides, like 4-chloromethylbenzoate or 4-chlorocyanobenzene. Surprisingly, the use of less activated aryl chlorides, like 4-chloroacetophenone, leads to the formation of dimethyl terephthalate amongst other products arising from organic reactions of methoxide ion and/or CO. Less nucleophilic alcohols such as 2,2,2-trifluoroethanol promote the formation of carbonylation products even from 4-chloroacetophenone and chlorobenzene. Labelling studies involving CD3OH, CD3OD or 13CO give information on the origin of many of the products.Keywords
This publication has 20 references indexed in Scilit:
- Development of new palladium catalysts for the alkoxycarbonylation of aryl chloridesJournal of Organometallic Chemistry, 2002
- A More Efficient Catalyst for the Carbonylation of ChloroarenesAngewandte Chemie International Edition, 2001
- Highly active and selective catalysts for the production of methyl propanoate via the methoxycarbonylation of etheneChemical Communications, 1999
- A practical convenient homogeneous palladium-phosphine catalysis for hydrocarbonylation of chlorobenzenesJournal of Molecular Catalysis A: Chemical, 1997
- Palladium-Catalyzed Carbonylation and Coupling Reactions of Aryl Chlorides and AminesThe Journal of Organic Chemistry, 1996
- Chelate effect on the structure and reactivity of electron-rich palladium complexes and its relevance to catalysisOrganometallics, 1993
- Mechanism of aryl chloride oxidative addition to chelated palladium(0) complexesOrganometallics, 1993
- An exceptionally simple biphasic method for the metal catalysed carbonylation of chloroarenesJournal of the Chemical Society, Chemical Communications, 1992
- Chelate-assisted, palladium-catalyzed efficient carbonylation of aryl chloridesJournal of the American Chemical Society, 1989
- Bi-metallic activation in homogeneous catalysis: palladium-catalysed carbonylation of tricarbonyl(chloroarene)chromium complexes to the corresponding aldehydes, esters, amides, and α-oxo amidesJournal of the Chemical Society, Chemical Communications, 1988