Issue 53, 2022
From the journal:

RSC Advances

Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines†

Fábio Z. Galetto, ORCID logo *a   Cleiton da Silva,a   Ricardo I. M. Beche,a   Renata A. Balaguez,a   Marcelo S. Franco, ORCID logo a   Francisco F. de Assis,a   Tiago E. A. Frizonb  and  Xiao Su ORCID logo c  

* Corresponding authors

a Department of Chemistry, Federal University of Santa Catarina, Florianópolis, SC, Brazil
E-mail: galetto.f.z@ufsc.br
Tel: +554837213649

b Department of Energy and Sustainability, Federal University of Santa Catarina, Araranguá, SC, Brazil

c Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, Urbana, IL, USA

Abstract

We report herein the synthesis of primary and secondary β-chalcogen amines through the regioselective ring-opening reaction of non-activated 2-oxazolidinones promoted by in situ generated chalcogenolate anions. The developed one-step protocol enabled the preparation of β-selenoamines, β-telluroamines and β-thioamines with appreciable structural diversity and in yields of up to 95%.

Graphical abstract: Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines

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Article information

DOI
https://doi.org/10.1039/D2RA06070A
Article type
Paper
Submitted
26 Sep 2022
Accepted
18 Nov 2022
First published
30 Nov 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 34496-34502

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Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines

F. Z. Galetto, C. da Silva, R. I. M. Beche, R. A. Balaguez, M. S. Franco, F. F. de Assis, T. E. A. Frizon and X. Su, RSC Adv., 2022, 12, 34496 DOI: 10.1039/D2RA06070A

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