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Environmental Chemistry Letters

, Volume 17, Issue 3, pp 1441–1446 | Cite as

Rice straw ash extract, an efficient solvent for regioselective hydrothiolation of alkynes

  • Marcelo GodoiEmail author
  • Andrielli Leitemberger
  • Lucas Martins Correa Böhs
  • Marcia Victoria Silveira
  • Jamal Rafique
  • Marcelo Gonçalves Montes D’Oca
Original Paper

Abstract

Herein, we describe a simple and inexpensive protocol for the hydrothiolation of alkynes. In this context, water extract of rice straw ash (WERSA) has been proven to be a green, mild and efficient solvent for the preparation of vinyl thioethers. Generally, it was found that alkyne and thiol derivatives were excellent reaction partners, producing the corresponding products with good yields and good stereoselectivity with the predominant formation of the Z isomer. Moreover, WERSA was recovered and reused for further catalytic reactions without a significant loss of activity.

Keywords

WERSA Hydrothiolation Alkynes Alkenes Thiols Agro-waste 

Notes

Acknowledgements

We gratefully acknowledge the National Council for Scientific and Technological Development—CNPq, CAPES and FAPERGS-Pronex for financial support. The authors are also grateful to CIA-FURG for the NMR analysis and the Program of Support for the Publication of Academic Production/PROPESP/FURG/2018. CAPES and PET-FURGSAP are also acknowledged for the fellowship for A. L. and L. M. C. B., respectively. Funding was provided by Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (Grant No FAPERGS/CNPq 12/2014 - PRONEX) and National Council for Scientific and Technological Development-CNPq (Grant No 428494/2018-8).

Supplementary material

10311_2019_882_MOESM1_ESM.doc (1.5 mb)
Supplementary material 1 (DOC 1562 kb)

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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Escola de Química e AlimentosUniversidade Federal do Rio Grande-Campus Santo Antônio da Patrulha - FURG – SAPSanto Antônio da PatrulhaBrazil
  2. 2.Instituto de QuímicaUniversidade Federal do Mato Grosso do Sul - UFMSCampo GrandeBrazil

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