Highlight on the reactivity of PhSeZnX

Bonifacio Monti; Luca Sancineto; Martina Palomba; Luana Bagnoli; Francesca Marini; Eder Lenardao; Claudio Santi

doi:10.3390/ecsoc-19-a002

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Highlight on the reactivity of PhSeZnX

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¹ Group of Catalysis Synthesis and Organic Green Chemistry (CS-ORG CHEM) - Department of Pharmaceutical Sciences - University of Perugia
² Universidade Federal de Pelotas (UFPel), P.O. Box 354, Pelotas 96010-900, Brazil

Published: 30 October 2015 by MDPI in The 19th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-19-a002

Abstract:

The first bench stable selenolates, PhSeZnHalides have been synthesized through a completely atom economy oxidative insertion of the elemental zinc on the commercially available PhSeHalides. These reagents showed the characteristic nucleophilic reactivity which will be reviewed in this report. All of the reactions were strongly accelerated when effected in water suspension. Alkyl, aryl, vinyl and acyl substitutions, ring-opening reactions of epoxides and aziridines and Michael type addition will be described including the role of the zinc in the control of the chemoselectivity and stereoselectivity.

Keywords: Selenium, Zinc, Nucleohpile, epoxide, Michael addition

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