Synlett 2009(10): 1690-1691  
DOI: 10.1055/s-0029-1217323
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Simmons-Smith Reagent (Et2Zn, CH2I2): An Efficient Reagent in Organic Synthesis

Ali Maleki*
Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran
e-Mail: a_maleki@sbu.ac.ir;
Further Information

Publication History

Publication Date:
02 June 2009 (online)

Introduction

The diethylzinc/diiodomethane or zinc-diiodomethane (Et2Zn, CH2I2 or Zn, CH2I2 = ICH2ZnI) known as Simmons-Smith reagent is probably the best known carbenoid reagent in organic syntheses. [¹] This ether soluble reagent has been used mainly for the conversion of al­kenes into cyclopropanes [¹] via stereospecific and supra­facial CH2 addition using chiral auxiliaries, [²] reagents [³] and catalysts. [4]

Due to the presence of cyclopropanes in many biologically and medicinally important molecules, [5] natural products, [6] essential oils [7] and the marine cyanobacteriums, [8] some recent applications of Simmons-Smith reagent are reported herein.

    References

  • 1a Simmons HE. Smith RD. J. Am. Chem. Soc.  1959,  81:  4256 
  • 1b Simmons HE. Smith RD. J. Am. Chem. Soc.  1958,  80:  5322 
  • 1c Charette AB. Beauchemin A. Simmons-Smith Cyclopropanation Reaction In Organic Reactions   John Wiley & Sons; New York: 2001.  58:  p.1-415  
  • 2 Kang J. Lim GJ. Yoon SK. Kim MY. J. Org. Chem.  1995,  60:  564 
  • 3 Charette AB. Juteau H. Lebel H. Molinaro C. J. Am. Chem. Soc.   1998,  120 :  11943 
  • 4 Balsells J. Walsh PJ. J. Org. Chem.  2000,  65:  5005 
  • 5 Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev.  2003,  103:  977 
  • 6 Wessjohann LA. Brandt W. Thiemann T. Chem. Rev.  2003,  103:  1625 
  • 7a Roberts IO. Baird MS. Liu Y. Tetrahedron Lett.  2004,  45:  8685 
  • 7b Cheeseman M. Bull SD. Synlett  2006,  1119 
  • 8 Avery TD. Culbert JA. Taylor DK. Org. Biomol. Chem.   2006,  4:  323 
  • 9 Shitama H. Katsuki T. Angew. Chem. Int. Ed.  2008,  47:  2450 
  • 10 Du H. Long J. Shi Y. Org. Lett.  2006,  8:  2827 
  • 11 White JD. Martin WHC. Lincoln C. Yang J. Org. Lett.  2007,  9:  3481 
  • 12 Davies SG. Ling KB. Roberts PM. Russell AJ. Thomson JE. Chem. Commun.  2007,   4029 
  • 13 Zhuo J. Burns DM. Zhang C. Xu M. Weng L. Qian D.-Q. He C. Lin Q. Li Y.-L. Shi E. Agrios C. Metcalf B. Yao W. Synlett  2007,  460 
  • 14 Song Z. Lu T. Hsung RP. Al-Rashid ZF. Ko C. Tang Y. Angew. Chem. Int. Ed.  2007,  46:  4069 
  • 15 Kim A. Hong JH. Eur. J. Med. Chem.  2007,  42:  487 
  • 16 Poverenov E. Milstein D. Chem. Commun.  2007,   3189 
  • 17 Salim H. Piva O. Tetrahedron Lett.  2007,  48:  2059