Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters

Ji Yang, Jiawang Liu, Yao Ge, Weiheng Huang, Francesco Ferretti, Helfried Neumann, Haijun Jiao, Robert Franke, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.

Original languageEnglish
Pages (from-to)9527-9533
Number of pages7
JournalAngewandte Chemie International Edition in English
Volume60
Issue number17
DOIs
StatePublished - 19 Apr 2021
Externally publishedYes

Keywords

  • adipates
  • aliphatic diesters
  • carbonylation
  • catalysis
  • dienes

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