Synlett 2012; 23(12): 1847-1848
DOI: 10.1055/s-0031-1290430
spotlight
© Georg Thieme Verlag Stuttgart · New York

Sodium Selenide

Rui-Yun Guo
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, P. R. of China, Email: [email protected]
› Author Affiliations
Further Information

Publication History

Publication Date:
05 July 2012 (online)

 
Zoom Image

Rui-Yun Guo was born in 1988 in Handan, Hebei Province, P. R. of China. She graduated from Hebei Normal University in 2011 and received her B.Sc. degree in Chemistry. Presently, she is working as a postgraduate towards her M.Sc. under the supervision of Professor Zhan-Hui Zhang at Hebei Normal University. Her research interest focuses on the development of new reagents and catalysts in organic synthesis.

Introduction

Sodium selenide is an odourless white crystalline solid, which is soluble in water. Sodium selenide is very useful in the preparation of a wide variety of selenium-containing heterocycles.[ 1 ] It can be used for the synthesis of substituted selenophenes, [2] [3] nitroxide annulated 3-amino-2-(ethoxycarbonyl)selenophene,[ 4 ] bis(2,4,6-trimethylphenyl)selenide,[ 5 ] phosphinodiselenoic acid salt,[ 6 ] unsaturated selenacrown ethers,[ 7 ] diselenobenzoquinone complexes,[ 8 ] and 1,4-dichalcogenanes.[ 9 ] In addition, it has been employed in the ring opening of epoxides[ 10 ] and γ-butyrolactones.[ 11 ]

Sodium selenide is commercially available and can be prepared by reduction of elemental selenium with sodium in liquid ammonia (Scheme [1]).[ 12 ]

Zoom Image
Scheme 1

#

Abstracts

(A) Synthesis of Functionalized Divinyl Selenides:
Potapov et al. have found that functionalized divinyl selenides can be synthesized by regio- and stereoselective addition of sodium selenide to ethynyl ketones.[ 13 ]

(B) Synthesis of Selenopyran-3-carboxamide Derivatives:
The [5+1]-annulation reactions of α-alkenoyl-α-carbamoylketene dithioacetals with Na2Se afforded highly functionalized selenopyran-3-carboxamide derivatives in high yields.[ 14 ]

(C) Synthesis of Dipropargyl Selenide:
Amosova et al. have developed a simple and efficient procedure for conversion of propargyl bromide into dipropargyl selenide.[ 15 ]

(D) Synthesis of 1-Thia-4-chalcogenacyclohexane-1-oxides and 1,1-Dioxides:
Potapov et al. reported that 1-thia-4-chalcogenacyclohexane-1-oxides and 1,1-dioxides can be obtained via the addition of sodium selenide to divinylsulfoxide and sulfone.[ 16 ]

(E) Synthesis of Substituted Selenophenes :
Sommen et al. reported a simple and efficient method for the synthesis of various substituted selenophenes. Selenophenes were successfully prepared from ketene dithioacetals and sodium selenide along with ethyl bromoacetate, chloroacetonitrile, chloroacetone and bromoacetophenone in moderate to good yields.[ 17 ]

(F) One-pot Synthesis of Substituted 3-Amino-2-nitroselenophenes:

One-pot synthesis of substituted 3-amino-2-nitroselenophenes has been achieved via a three-step procedure by using β-chloroacroleins, sodium selenide and bromonitromethane.[ 18 ]

(G) Synthesis of 2,4,5-Trisubstituted Selenazoles:
Thomae et al. reported that 2,4,5-trisubstituted selenazoles can be obtained by a one-pot, four-step procedure from azomethine dithioacetals.[ 19 ]

(H) Synthesis of 2,3,4-Substituted Selenophenes:
2,3,4-Trisubstituted selenophenes can also be synthesized by a Fiesselmann’s reaction implying a β-chloroacrolein, sodium selenide and an alkyl bromoacetate.[ 20 ]


#
#
  • References

  • 1 Sommen GL, Thomae D. Curr. Org. Synth. 2010; 7: 44
  • 2 Rhoden CR. B, Zeni G. Org. Biomol. Chem. 2011; 9: 1301
  • 3 Thomae D, Kirsch G, Seck P. Synthesis 2008; 1600
  • 4 Kálai T, Bagi N, Jekő J, Berente Z, Hideg K. Synthesis 2010; 1702
  • 5 Ghavale N, Phadnis PP, Wadawale A, Jain VK. Indian J. Chem. 2011; 50A: 22
  • 6 Kimura T, Murai T. J. Org. Chem. 2005; 70: 952
  • 7 Shimizu T, Kawaguchi M, Tsuchiya T, Hirabayashi K, Kamigata N. J. Org. Chem. 2005; 70: 5036
  • 8 Amouri H. Synlett 2011; 1357
  • 9 Martynov AV, Larina LI, Amosova SV. Tetrahedron Lett. 2012; 53: 1218
  • 10 Scianowski J, Rafinski Z, Wojtczak A, Burczynski K. Tetrahedron: Asymmetry 2009; 20: 2871
  • 11 Krief A, Derock M. Synlett 2005; 1012
  • 12 Woollins JD. Synlett 2012; 1154
  • 13 Potapov VA, Elokhina VN, Larina LI, Yaroshenko TI, Tatarinova AA, Amosova SV. J. Organomet. Chem. 2009; 694: 3679
  • 14 Li DW, Xu XX, Liu Q, Dong S. Synthesis 2008; 1895
  • 15 Amosova SV, Martynov AV. Russ. J. Org. Chem. 2011; 47: 1772
  • 16 Potapov VA, Amosova SV, Doron’kina IV, Korsun OV. J. Organomet. Chem. 2003; 674: 104
  • 17 Sommen G, Comel A, Kirsch G. Synlett 2003; 855
  • 18 Thomae D, Dominguez JC. R, Kirsch G, Seck P. Tetrahedron 2008; 64: 3232
  • 19 Thomae D, Perspicace E, Henryon D, Xu ZJ, Schneider S, Hesse S, Kirsch G, Seck P. Tetrahedron 2009; 65: 10453
  • 20 Sommen GL. Mini-Rev. Org. Chem. 2005; 2: 375

  • References

  • 1 Sommen GL, Thomae D. Curr. Org. Synth. 2010; 7: 44
  • 2 Rhoden CR. B, Zeni G. Org. Biomol. Chem. 2011; 9: 1301
  • 3 Thomae D, Kirsch G, Seck P. Synthesis 2008; 1600
  • 4 Kálai T, Bagi N, Jekő J, Berente Z, Hideg K. Synthesis 2010; 1702
  • 5 Ghavale N, Phadnis PP, Wadawale A, Jain VK. Indian J. Chem. 2011; 50A: 22
  • 6 Kimura T, Murai T. J. Org. Chem. 2005; 70: 952
  • 7 Shimizu T, Kawaguchi M, Tsuchiya T, Hirabayashi K, Kamigata N. J. Org. Chem. 2005; 70: 5036
  • 8 Amouri H. Synlett 2011; 1357
  • 9 Martynov AV, Larina LI, Amosova SV. Tetrahedron Lett. 2012; 53: 1218
  • 10 Scianowski J, Rafinski Z, Wojtczak A, Burczynski K. Tetrahedron: Asymmetry 2009; 20: 2871
  • 11 Krief A, Derock M. Synlett 2005; 1012
  • 12 Woollins JD. Synlett 2012; 1154
  • 13 Potapov VA, Elokhina VN, Larina LI, Yaroshenko TI, Tatarinova AA, Amosova SV. J. Organomet. Chem. 2009; 694: 3679
  • 14 Li DW, Xu XX, Liu Q, Dong S. Synthesis 2008; 1895
  • 15 Amosova SV, Martynov AV. Russ. J. Org. Chem. 2011; 47: 1772
  • 16 Potapov VA, Amosova SV, Doron’kina IV, Korsun OV. J. Organomet. Chem. 2003; 674: 104
  • 17 Sommen G, Comel A, Kirsch G. Synlett 2003; 855
  • 18 Thomae D, Dominguez JC. R, Kirsch G, Seck P. Tetrahedron 2008; 64: 3232
  • 19 Thomae D, Perspicace E, Henryon D, Xu ZJ, Schneider S, Hesse S, Kirsch G, Seck P. Tetrahedron 2009; 65: 10453
  • 20 Sommen GL. Mini-Rev. Org. Chem. 2005; 2: 375

Zoom Image
Zoom Image
Scheme 1