Synlett 2025; 36(10): 1408-1412
DOI: 10.1055/a-2527-1554
letter

Improving the Performance of Palladium-Catalyzed Telomerization of 1,3-Butadiene with Malonate by Alcohol Solvent

Xuan Chen
a   State Key Laboratory of Molecular & Process Engineering & Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
,
Chaoren Shen
a   State Key Laboratory of Molecular & Process Engineering & Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
,
Kaiwu Dong
a   State Key Laboratory of Molecular & Process Engineering & Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
b   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
› Author Affiliations

This work was financially supported by the National Nature Science Foundation of China (22271094), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0610000), the Innovation Program of the Shanghai Municipal Education Commission (2023ZKZD37), and the Fundamental Research Funds for the Central Universities.


Abstract

Using alcohol instead of largely excessive malonate as the solvent can improve the performance of palladium-catalyzed telomerization of 1,3-butadiene with malonate. Under the basic conditions, the main reaction was not overwhelmed by the telomerization of 1,3-butadiene with methanol solvent. With this method, methyl (E)-deca-4,9-dienoate, the intermediate for the synthesis of 10-hydroxy decanoic acid, undecanedioic acid, and 11-hydroxy undecanoic acid, can be prepared from the telomerization of 1,3-butadiene with dimethyl malonate in good yield.

Supporting Information



Publication History

Received: 15 January 2025

Accepted after revision: 28 January 2025

Accepted Manuscript online:
28 January 2025

Article published online:
12 March 2025

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