Palladium-catalyzed alkoxycarbonylation of conjugated dienes under acid-free conditions: Atom-economic synthesis of β,γ-unsaturated esters

Xianjie Fang, Haoquan Li, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Carbonylation reactions constitute important methodologies for the synthesis of all kinds of carboxylic acid derivatives. The development of novel and better catalysts for these transformations is of interest for both academic and industrial research. Here, a benign palladium-based catalyst system for the alkoxycarbonylation of conjugated dienes under acid-free conditions has been developed. This atom-efficient transformation provides straightforward access to a variety of β,γ-unsaturated esters in good to excellent yields and often with high selectivities. As an industrially relevant example the (formal) synthesis of dimethyl adipate and ε-caprolactam from 1,3-butadiene is demonstrated.

Original languageEnglish
Pages (from-to)9030-9034
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume53
Issue number34
DOIs
StatePublished - 18 Aug 2014
Externally publishedYes

Keywords

  • P ligands
  • carbonylation
  • conjugation
  • palladium
  • synthetic methods

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