Issue 82, 2022

Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents

Abstract

Once considered to be exotic species of limited synthetic utility, vinyl cations have recently been shown to be highly versatile intermediates in a variety of processes. Here, we report a method for the synthesis of aryl-substituted benzocycloheptenes and -hexenes using the hydrotriflate salt of an electron-poor pyridine as a uniquely efficient proton source for a vinyl cation mediated Friedel–Crafts cyclization. The mild conditions made possible by this reagent allowed a range of simple and functionalized alkynes bearing pendant aryl groups to serve as suitable substrates for this scalable and convenient protocol.

Graphical abstract: Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents

Supplementary files

Article information

Article type
Communication
Submitted
07 7 2022
Accepted
13 9 2022
First published
13 9 2022

Chem. Commun., 2022,58, 11523-11526

Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents

J. C. Corcoran, R. Guo, Y. Xia and Y. Wang, Chem. Commun., 2022, 58, 11523 DOI: 10.1039/D2CC03794G

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