Green Michael addition of thiols to electron deficient alkenes using KF/alumina and recyclable solvent or solvent-free conditions

Journal of the Brazilian Chemical Society

Eder J. Lenardão²  Danusia O. Trecha¹  Patrícia Da C. Ferreira¹  Raquel G. Jacob¹  Gelson Perin¹ 

[1] ,Universidade Federal de Pelotas Instituto de Química e Geociências Pelotas RS ,Brazil

关键词: solvent-free;    1;    4-addition of thiols;    glycerin;    citral and citronellal;    green chemistry;   

DOI  :  10.1590/S0103-50532009000100016

来源: SciELO

【 摘 要 】

A general, clean and easy method for the conjugated addition of thiols to citral promoted by KF/Al2O3 under solvent-free or using glycerin as recyclable solvent at room temperature is described. It was found that the solvent-free protocol is applicable to the direct reaction of thiophenol with the essential oil of lemon grass (Cymbopogon citratus) to afford directly 3,7-dimethyl-3-(phenylthio)oct-6-enal, a potential bactericide agent. The method was extended to other electron-poor alkenes with excellent results. For the solvent-free protocol, the use of microwave irradiation facilitated the procedure and accelerates the reaction. The catalytic system and glycerin can be reused up to three times without previous treatment with comparable activity.

【 授权许可】

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