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

Journal of the American Chemical Society
Jiawang LiuMatthias Beller

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.

References

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May 12, 2009·Angewandte Chemie·Anne BrennführerMatthias Beller
Jul 11, 2009·Angewandte Chemie·Katrin Marie DrillerMatthias Beller
Oct 9, 2012·Chemical Reviews·Xiao-Feng WuMatthias Beller
Feb 13, 2014·Nature Communications·Lipeng WuMatthias Beller
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Jan 26, 2017·Nature Communications·Kaiwu DongMatthias Beller
Apr 22, 2017·Angewandte Chemie·Kaiwu DongMatthias Beller
Mar 13, 2018·Journal of the American Chemical Society·Rui SangMatthias Beller

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Citations

Oct 13, 2018·Chemical Communications : Chem Comm·Jiawang LiuMatthias Beller
Apr 10, 2020·Chemical Communications : Chem Comm·Ji YangMatthias Beller
May 3, 2019·Chemical Communications : Chem Comm·Shaoke ZhangMatthias Beller
Sep 23, 2020·Angewandte Chemie·Jiawang LiuMatthias Beller
Dec 17, 2020·Angewandte Chemie·Duanshuai TianWenjun Tang
Jul 29, 2021·Physical Chemistry Chemical Physics : PCCP·Shahbaz Ahmad, Michael Bühl

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