Synlett 2012; 23(19): 2865-2866
DOI: 10.1055/s-0032-1317475
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© Georg Thieme Verlag Stuttgart · New York

Phenylselenyl Zinc Halides

Caterina Tidei
Department of Chemistry and Technology of Drugs, University of Perugia, Via del Liceo 1, 06134 Perugia, Italy   Email: tideicaterina@gmail.com
› Author Affiliations
Further Information

Publication History

Publication Date:
31 October 2012 (online)

Introduction

Santi et al.[ 1 ] first isolated phenylselenyl zinc halides as bench-stable selenolates. They are versatile nucleophilic reagents, especially in ‘on water’ conditions, where they have been used for the synthesis of a large number of organoseleno compounds.[ 2 ] Furthermore, they also show interesting features from a biochemical and pharmaceutical point of view because of the unusual stabilized oxidation state of selenium, the same of the selenium atom present in the catalytic site of some selenoenzymes. On the basis of this, recently a Gpx-like activity for PhSeZnCl has been demonstrated.[ 3 ]

 
  • References

  • 1 Santi C, Santoro S, Battistelli B, Testeferri L, Tiecco M. Eur. J. Org. Chem. 2008; 5387
  • 2 Santi C. Phenylselenenylzinc halides . In Encyclopaedia of Reagents for Organic Synthesis . Paquette LA. John Wiley & Sons; New York: DOI: 10 1002/047084289X.rn01352
  • 3 Tidei C, Piroddi M, Galli F, Santi C. Tetrahedron Lett. 2012; 232
  • 4 Santoro S, Battistelli B, Testaferri L, Tiecco M, Santi C. Eur. J. Org. Chem. 2009; 4921
  • 5 Salman SM, Schwab RS, Alberto EE, Vargas J, Dornelles L, Rodrigues OE. D, Braga AL. Synlett 2011; 69
  • 6 Santi C, Battistelli B, Testaferri L, Tiecco M. Green Chem. 2012; 1277
  • 7 Battistelli B, Testaferri L, Tiecco M, Santi C. Eur. J. Org. Chem. 2011; 1848