Facile synthesis of amides via acceptorless dehydrogenative coupling of aryl epoxides and amines

Yaoyu Liang, Jie Luo, David Milstein*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)
36 Downloads (Pure)

Abstract

The synthesis of amides is significant in a wide variety of academic and industrial fields. We report here a new reaction, namely acceptorless dehydrogenative coupling of epoxides and amines to form amides catalyzed by ruthenium pincer complexes. Various aryl epoxides and amines smoothly convert into the desired amides in high yields with the generation of H-2 gas as the only byproduct. Control experiments indicate that amides are generated kinetically faster than side products, possibly because of the facile activation of epoxides by metal-ligand cooperation, as supported by the observation of a ruthenium-enolate species. No alcohol or free aldehyde are involved. A mechanism is proposed involving a dual role of the catalyst, which is responsible for the high yield and selectivity of the new reaction.
Original languageEnglish
Pages (from-to)5913-5919
Number of pages7
JournalChemical science (Cambridge)
Volume13
Issue number20
Early online date26 Apr 2022
DOIs
Publication statusPublished - 28 May 2022

Funding

This research was supported by the European Research Council (ERC AdG 692775). D. M. holds the Israel Matz Professorial Chair of Organic Chemistry. J. L. is thankful to the Feinberg Graduate School of Weizmann Institute of Science for a Senior Postdoctoral Fellowship.

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