Issue 22, 2017

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1 : 1 ratio under solvent-free conditions

Abstract

A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1 : 1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C–Br as well as C[double bond, length as m-dash]C and C[triple bond, length as m-dash]C bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.

Graphical abstract: Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1 : 1 ratio under solvent-free conditions

Supplementary files

Article information

Article type
Paper
Submitted
19 iyl 2017
Accepted
16 avq 2017
First published
16 avq 2017

Green Chem., 2017,19, 5396-5402

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1 : 1 ratio under solvent-free conditions

Z. Tang, Q. Jiang, L. Peng, X. Xu, J. Li, R. Qiu and C. Au, Green Chem., 2017, 19, 5396 DOI: 10.1039/C7GC02174G

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