Azodioxy Compounds as Precursors for C-Radicals and Their Application in Thermal Styrene Difunctionalization

Abstract

An atom-economic thermal α,β-difunctionalization of various styrenes with readily prepared azodioxy compounds is reported. Mechanistic studies reveal that the starting azodioxy compounds can thermally be cleaved to the corresponding C-nitroso compounds, which under these thermal conditions further homolyze to generate reactive C-radicals along with the persistent NO radical. In the presence of a styrene, C-radical addition with subsequent nitrosylation followed by tautomerization is occurring, resulting in an overall styrene β-alkylation-α-oximation reaction.

Article information

Article type
Edge Article
Submitted
11 Jul 2022
Accepted
03 Aug 2022
First published
05 Aug 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022, Accepted Manuscript

Azodioxy Compounds as Precursors for C-Radicals and Their Application in Thermal Styrene Difunctionalization

S. Plöger, C. Mück-Lichtenfeld, C. G. Daniliuc and A. Studer, Chem. Sci., 2022, Accepted Manuscript , DOI: 10.1039/D2SC03860A

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