Rapid and One-Pot Synthesis of Aryl Ynamides from Aryl Alkynyl Acids by Metal-Free C-N Cleavage of Tertiary Amines

TL;DR

This paper presents a fast and efficient method to make aryl ynamides without using metals, offering a practical and eco-friendly alternative.

Contribution

The novel approach uses metal-free C-N cleavage of tertiary amines to synthesize aryl ynamides efficiently.

Findings

The method produced aryl ynamides with medium to excellent yields (up to 95%) in 33 examples.

The reaction is more efficient than traditional stepwise methods using secondary amines.

The process is scalable and environmentally benign.

Abstract

Herein a rapid, metal-free, and highly efficient synthesis of aryl ynamides from aryl alkynyl acids has been described. This approach, utilizing tertiary amines as an amino source via metal-free C-N cleavage, enabled the construction of a diverse range of aryl ynamides with medium to excellent yields (33 examples, up to 95% yield). This reaction exhibits significantly enhanced efficiency compared to the conventional stepwise approach involving aryl alkynyl acids and secondary amines. It can be successfully scaled up, providing a practical and environmentally benign strategy for alkynamide synthesis.

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