Issue 12, 2021

Silica gel-induced aryne generation from o-triazenylarylboronic acids as stable solid precursors

Abstract

We report the development of o-triazenylarylboronic acids as new aniline-based aryne precursors. The readily available and shelf-stable solid precursors generate (hetero)arynes under remarkably mild conditions using silica gel as the sole reagent, which subsequently undergo reactions with a range of arynophiles. Furthermore, solid-state aryne reactions under solvent-free conditions were accomplished. Aryne generation proceeded via a dual activation mechanism, as rationalized using Jaffé's plot analysis based on Hammett constants.

Graphical abstract: Silica gel-induced aryne generation from o-triazenylarylboronic acids as stable solid precursors

Supplementary files

Article information

Article type
Research Article
Submitted
10 mar 2021
Accepted
27 mar 2021
First published
09 apr 2021
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2021,8, 2963-2969

Silica gel-induced aryne generation from o-triazenylarylboronic acids as stable solid precursors

M. Ito, Y. Yamabayashi, M. Oikawa, E. Kano, K. Higuchi and S. Sugiyama, Org. Chem. Front., 2021, 8, 2963 DOI: 10.1039/D1QO00385B

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