Issue 38, 2024

Modular synthesis of aryl amines from 3-alkynyl-2-pyrones

Abstract

The synthesis of aryl amines from 3-alkynyl-2-pyrones and various amines is described. Mechanistically, the aryl amines are proposed to arise from the 3-alkynyl-2-pyrone substrates through their selective opening in a 1,6-fashion by secondary amines followed by decarboxylation and an unexpected rearrangement. The proposed mechanism is supported by quantum chemical transition-state calculations, which are consistent with the regiochemical outcome. The scope of this transformation spans a variety of 3-alkynyl-2-pyrones and a range of secondary amines. The influence of the secondary amine coupling partners on reaction efficiency was elucidated through data-driven modeling as well as scope exploration. These latter studies revealed that the steric bulk of the secondary amine coupling partner under the reaction conditions serves as a strong indicator of overall reaction efficiency.

Graphical abstract: Modular synthesis of aryl amines from 3-alkynyl-2-pyrones

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Jul 2024
Accepted
30 Aug 2024
First published
30 Aug 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 15632-15638

Modular synthesis of aryl amines from 3-alkynyl-2-pyrones

K. E. Gardner, L. de Lescure, M. A. Hardy, J. Tan, M. S. Sigman, R. S. Paton and R. Sarpong, Chem. Sci., 2024, 15, 15632 DOI: 10.1039/D4SC04885G

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