Oxoarylation of ynamides with N-aryl hydroxamic acids

Ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis. Therefore, the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting. Herein, we report an oxoarylation of ynamides with N-aryl hydroxamic acids. In the presence of catalytic Cu(OTf)(2), both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic acids to achieve oxoarylation, along with providing selective entry to (ortho-amino)arylacetamides and oxindoles. Moreover, deuterium-labelling reaction and gram-scale reaction were conducted to probe the mechanism and showcase the scalability. (C) 2021 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

Automated summary

This study demonstrates the oxoarylation of ynamides with N-aryl hydroxamic acids, and probes the mechanism and scalability through deuterium-labelling reaction and gram-scale reaction.