Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters

Jiawang Liu, Kaiwu Dong, Robert Franke, Helfried Neumann, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

57 Scopus citations

Abstract

A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.

Original languageEnglish
Pages (from-to)10282-10288
Number of pages7
JournalJournal of the American Chemical Society
Volume140
Issue number32
DOIs
StatePublished - 15 Aug 2018
Externally publishedYes

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