Synthesis 2019; 51(21): 4014-4022
DOI: 10.1055/s-0037-1611913
paper
© Georg Thieme Verlag Stuttgart · New York

Cobalt Used as a Novel and Reusable Catalyst: A New and One-Pot Synthesis of Isatin-Derived N,S-Acetals Using Substituted Isatins and Thiols

Caren D. G. da Silva
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
,
Ramesh Katla
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
,
Beatriz F. dos Santos
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
,
José M. C. Tavares Junior
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
,
Tábata B. Albuquerque
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
,
Vicente L. Kupfer
b  Material Chemistry and Sensores Laboratory - LMSen, State University of Maringá, Maringá/PR, Brazil
,
Andrelson W. Rinaldi
b  Material Chemistry and Sensores Laboratory - LMSen, State University of Maringá, Maringá/PR, Brazil
,
a  Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados - UFGD, Dourados/MS, Brazil   eMail: nelsondomingues@ufgd.edu.br
› Institutsangaben
The authors N.L.C.D. and R.K. (Visiting Professor-Edital PROPP/UFGD) thank the Fundação de Apoio ao Desenvolvimento do Ensino, Ciência e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT/Brazil) (Chamada FUNDECT/CNPq Nº 15/2014 – PRONEM-MS), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq-307783/2017-0-Bolsas de Produtividade em Pesquisa - PQ), and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES 23038.008241/2014-89 - CAPES-FAPCO) for financial support.
Weitere Informationen

Publikationsverlauf

Received: 31. Mai 2019

Accepted after revision: 26. Juli 2019

Publikationsdatum:
21. August 2019 (online)

Abstract

The synthesis of isatin-derived N,S-acetals using cobalt as a recyclable heterogeneous catalyst in batch and continuous flow is reported for the first time. The present protocol produced high yields, which can be observed from the reaction between ketimines and thiols. Such reactions can also be applied to a gram-scale. In addition, the catalyst is recyclable, economically-viable, and nontoxic as well as easy to prepare. The remarkable features of this new methodology are high conversion and cleaner reaction profiles.

Supporting Information

 
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