Magic of alpha: the chemistry of a remarkable bidentate phosphine, 1,2-bis(di-tert-butylphosphinomethyl)benzene

Johanna Vondran, Marc R L Furst, Graham R Eastham, Thomas Seidensticker, David J Cole-Hamilton

Research output: Contribution to journalReview articlepeer-review

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Abstract

The bidentate phosphine ligand 1,2-bis(di-tert-butylphosphinomethyl)benzene (1,2-DTBPMB) has been reported over the years as being one of, if not the, best ligands for achieving the alkoxycarbonylation of various unsaturated compounds. Bonded to palladium, the ligand provides the basis for the first step in the commercial (Alpha) production of methyl methacrylate as well as very high selectivity to linear esters and acids from terminal or internal double bonds. The present review is an overview covering the literature dealing with the 1,2-DTBPMB ligand: from its first reference, its catalysis, including the alkoxycarbonylation reaction and its mechanism, its isomerization abilities including the highly selective isomerizing methoxycarbonylation, other reactions such as cross-coupling, recycling approaches, and the development of improved, modified ligands, in which some tert-butyl ligands are replaced by 2-pyridyl moieties and which show exceptional rates for carbonylation reactions at low temperatures.
Original languageEnglish
Pages (from-to)6610-6653
JournalChemical Reviews
Volume121
Issue number11
Early online date7 May 2021
DOIs
Publication statusPublished - 9 Jun 2021

Keywords

  • Hydrocarbons
  • Organic compounds
  • Alkyls
  • Ligands
  • Selectivity

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