Synlett 2024; 35(08): 908-914
DOI: 10.1055/s-0042-1751485
cluster
Special Issue dedicated to Keith Fagnou

Nickel-Catalyzed Transesterification of Methyl Esters

Yan-Long Zheng
a   Tianjin Key Laboratory of Drug Targeting and Bioimaging, Life and Health Intelligent Research Institute, Tianjin University of Technology, Tianjin, 300384, P. R. of China
b   Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada
,
Omid Daneshfar
b   Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada
,
Jia-Yi Li
a   Tianjin Key Laboratory of Drug Targeting and Bioimaging, Life and Health Intelligent Research Institute, Tianjin University of Technology, Tianjin, 300384, P. R. of China
,
Jeanne Masson-Makdissi
b   Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada
,
Émile Pinault-Masson
b   Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada
,
Stephen G. Newman
b   Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada
› Author Affiliations
Financial support for this work was provided by the Natural Sciences and Engineering Research Council of Canada (Grant No. RGPIN-2020-05065), the Canada Research Chairs Program (Grant No. 950-232650), and the National Natural Science Foundation of China (Grant No. 22101203). The Canada Foundation for Innovation and the Ontario Ministry of Research, Innovation and Science are thanked for essential infrastructure. We also thank the start-up funds from Tianjin University of Technology. J.M.-M. thanks the Natural Sciences and Engineering Research Council of Canada for a Canada Graduate Scholarship–Masters fellowship.


Dedicated to the late Prof. Keith Fagnou on the 20th anniversary of the start of his academic career.

Abstract

A transesterification of methyl esters with aliphatic alcohols was developed using Ni/dcype catalysis. This reaction features the cleavage of the strong C(acyl)–OMe bond in the absence of acidic or basic additives, providing volatile methanol as the only stoichiometric waste product. A wide range of (hetero)aromatic and aliphatic methyl esters can be converted into the corresponding functionalized esters in good to excellent yields with high efficiency. Compared with traditional transesterifications, this cross-coupling approach offers new opportunities for efficient and chemoselective synthesis.

Supporting Information



Publication History

Received: 02 June 2023

Accepted after revision: 10 July 2023

Article published online:
04 September 2023

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