Jump to main content
Jump to site search

Issue 4, 2021
Previous Article Next Article

Reactivity of ynamides in catalytic intermolecular annulations

Author affiliations

Abstract

Ynamides are unique alkynes with a carbon–carbon triple bond directly attached to the nitrogen atom bearing an electron-withdrawing group. The alkyne is strongly polarized by the electron-donating nitrogen atom, but its high reactivity can be finely tempered by the electron-withdrawing group. Accordingly, ynamides are endowed with both nucleophilic and electrophilic properties and their chemistry has been an active research field. The catalytic intermolecular annulations of ynamides, featuring divergent assembly of structurally important amino-heterocycles in a regioselective manner, have gained much attention over the past decade. This review aims to provide a comprehensive summary of the advances achieved in this area involving transition metal and acid catalysis. Moreover, the intermolecular annulations of ynamide analogs including ynol ethers and thioalkynes are also discussed, which can provide insights into the reactivity difference caused by the heteroatoms.

Graphical abstract: Reactivity of ynamides in catalytic intermolecular annulations

Back to tab navigation

Article information


Submitted
08 May 2020
First published
24 Dec 2020

Chem. Soc. Rev., 2021,50, 2582-2625
Article type
Review Article

Reactivity of ynamides in catalytic intermolecular annulations

Y. Hu, Y. Zhao, B. Wan and Q. Chen, Chem. Soc. Rev., 2021, 50, 2582
DOI: 10.1039/D0CS00283F

Social activity

Search articles by author

Spotlight

Advertisements