Issue 24, 2020

Brønsted acid-mediated reactions of ynamides

Abstract

Over the past two decades, the development and application of ynamide chemistry have received more and more attention. Ynamides have proven to be versatile reagents for organic synthesis, and have been widely applied to the rapid assembly of a diverse range of structurally complex N-containing molecules, especially the valuable N-heterocycles. In comparison with the well-established transition metal-catalyzed reactions of ynamides, metal-free ynamide transformations have relatively seldom been exploited. Recently, Brønsted acid-mediated reactions of ynamides represent significant advances in ynamide chemistry. This review summarizes the latest trends and developments of Brønsted acid-mediated reactions of ynamides, including cycloaddition, cyclization, intramolecular alkoxylation-initiated rearrangement, oxygen atom transfer reactions and hydro-heteroatom addition reactions.

Graphical abstract: Brønsted acid-mediated reactions of ynamides

Article information

Article type
Tutorial Review
Submitted
04 Aug. 2020
First published
02 Nov. 2020

Chem. Soc. Rev., 2020,49, 8897-8909

Brønsted acid-mediated reactions of ynamides

Y. Chen, P. Qian and L. Ye, Chem. Soc. Rev., 2020, 49, 8897 DOI: 10.1039/D0CS00474J

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