Synlett 2024; 35(13): 1545-1550
DOI: 10.1055/a-2205-5806
letter

Silver Nitrate Catalyzed Sulfonylation of O-Propargyl Alkynes

a   Universidade Federal de Pernambuco, Departamento de Química Fundamental, Av. Jorn. Aníbal Fernandes, s/n - Cidade Universitária, Recife , PE, 50740-560, Brazil
,
b   Universidade de São Paulo, Instituto de Física, Av. Trab. São Carlense, 400 - Parque Arnold Schimidt, São Carlos, SP, 13566-590, Brazil
,
a   Universidade Federal de Pernambuco, Departamento de Química Fundamental, Av. Jorn. Aníbal Fernandes, s/n - Cidade Universitária, Recife , PE, 50740-560, Brazil
,
c   Universidade Federal de Pernambuco, Colégio de Aplicação, Av. da Arquitetura, s/n - Cidade Universitária, Recife, PE, 50740-550, Brazil
,
a   Universidade Federal de Pernambuco, Departamento de Química Fundamental, Av. Jorn. Aníbal Fernandes, s/n - Cidade Universitária, Recife , PE, 50740-560, Brazil
,
a   Universidade Federal de Pernambuco, Departamento de Química Fundamental, Av. Jorn. Aníbal Fernandes, s/n - Cidade Universitária, Recife , PE, 50740-560, Brazil
› Author Affiliations
We gratefully acknowledge the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Grant Numbers 302829/2022-9 and 405052/2021-9), and the Fundação de Amparo à Ciência e Tecnologia do Estado de Pernambuco (FACEPE, Grant Numbers APQ-0436-1.06/22, IBPG-0009-1.06/19, and BFP-0039-1.06/22) for financial support.


Abstract

The development of new catalytic methods based on lower-cost metals under environmentally friendly conditions is still a challenge. Herein, we report an efficient strategy for the synthesis of vinyl sulfones from O-propargyl alkynes and sodium salts of sulfinic acids using silver nitrate, an inexpensive and readily available catalyst, under air atmosphere using aqueous conditions. The products were obtained in good to moderate yields, and the mechanism of the reaction was also investigated.

Supporting Information

Primary Data



Publication History

Received: 02 August 2023

Accepted after revision: 07 November 2023

Accepted Manuscript online:
07 November 2023

Article published online:
14 December 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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