Synlett 2011(11): 1638-1639  
DOI: 10.1055/s-0030-1260781
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Samarium Triiodide

Yuanmin Zhang*
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China
e-Mail: zym913@126.com;

Further Information

Publication History

Publication Date:
10 June 2011 (online)

Biographical Sketches

Yuanmin Zhang was born in Gansu, P. R. of China and received her B.Sc. degree (2009) in Chemistry from Tianshui Normal University. She is currently pursuing her M.Sc. degree under the supervision of associate professor Dr. Zhengyin Du at the College of Chemistry and Chemical Engineering, Northwest Normal University. Her research interests focus on the development of new synthetic methodologies for green chemistry.

Introduction

Samarium triiodide (SmI3) is a yellow powder with a melting point of 820 ˚C, unstable towards air and moisture. It is commercially available and has been widely used in organic reactions, such as elimination, conjugate addition, carbonyl reduction, intramolecular cyclization and nucleophilic substitution reactions. It can also be regarded as an efficient metal catalyst and a Lewis acid catalyst to accelerate reactions and to improve yields for organic transformations. Herein, the applications of SmI3 in recent years are listed and reviewed.

Abstracts

(A) A novel and highly efficient method for the conjugate addition of indoles with electron-deficient olefins catalyzed by SmI3 afforded a series of new 3-substituted indole derivatives. [¹] [²] This reaction is highly regioselective and can be accelerated by microwave irradiation with silica gel as catalyst support. [³]

(B) The Michael reaction of β-diketones with α,β-unsaturated esters catalyzed by samarium triiodide was achieved in THF under reflux to give the corresponding δ-carbonyl esters in good yields. [4]

(C) The nucleophilic substitution reaction between N-(1-benzotriazol-1-ylalkyl)amides and 1,3-dicarbonyl compounds promoted by samarium triiodide was reported. This provides a useful method for the preparation of Mannich-type products with good yields and high ­diastereoselectivities. [5]

(D) Catalyzed by SmI3, a series of arylamines reacted with dihydropyran to give pyrano[3,2-c]quinoline derivatives in moderate to good yields with high trans diastereoselectivity. [6]

(E) A simple methodology to prepare (E)-α-hydroxy-β,γ-unsaturated amides from α,β-epoxyamides, by using catalytic samarium triiodide, has been developed. This elimination reaction proceeds with total or high diastereoselectity and regioselectivity. [7]

(F) 1,1-Diacetates undergo deprotection and condensation reaction with cycloalkanones in the presence of catalytic samarium triiodide to afford α,α′-bis(substituted benzylidene)cycloalkanones in good yields. [8]

(G) A new and facile method to prepare (Z)-allylic iodides 2 from the acetates of Baylis-Hillman adducts 1 mediated by samarium triiodide was developed in ionic liquid [bmim]BF4 with excellent yields and good stereoselectivity. [9]

(H) A novel, one-pot three-component reaction of aldehydes, α-halo ketones and (phenylsulfonyl)acetonitrile was achieved in good yields in the presence of samarium triiodide. [¹0]

(I) SmI3-promoted β-elimination reactions of α-chloro-β-hydroxy ketones offer a highly efficient way to synthesize α,β-unsaturated ketones in good yields and E-diastereoselectivity. [¹¹]

(J) Samarium triiodide can also be used for the catalytic reduction of the saturated steroidal ketone into the corresponding secondary alcohol. [¹²]

    References

  • 1 Zhan ZP. Yang RF. Lang K. Tetrahedron Lett.  2005,  46:  3859 
  • 2 Zou XF. Wang XX. Cheng CG. Kong LC. Mao H. Tetrahedron Lett.  2006,  47:  3767 
  • 3 Zhan ZP. Lang K. Synlett  2005,  1551 
  • 4 Chen XY. Bao WL. Zhang YM. Chin. Chem. Lett.  2000,  11:  483 
  • 5 Wang XX. Mao H. Yu Y. Zhu XD. Zhu CL. Synth. Commun.  2007,  37:  3751 
  • 6 Yao LB. Xu F. Shen Q. Chinese Sci. Bull.  2010,  55:  4108 
  • 7 Concellon JM. Bernad PL. Bardales E. Chem. Eur. J.  2004,  10:  2445 
  • 8 Wang XX. Zhang YM. Chin. Chem. Lett.  2004,  15:  511 
  • 9 Liu YK. Zheng H. Xu DQ. Xu ZY. Zhang YM.
    J. Zhejiang Univ. Sci. B.  2006,  7:  193 
  • 10 Fan XS. Zhang YM. Chin. Chem. Lett.  2002,  13:  285 
  • 11 Concellon JM. Huerta M. Tetrahedron Lett.  2003,  44:  1931 
  • 12 Stastna E. Cerny I. Pouzar V. Chodounska H. Steroids  2010,  75:  721 

    References

  • 1 Zhan ZP. Yang RF. Lang K. Tetrahedron Lett.  2005,  46:  3859 
  • 2 Zou XF. Wang XX. Cheng CG. Kong LC. Mao H. Tetrahedron Lett.  2006,  47:  3767 
  • 3 Zhan ZP. Lang K. Synlett  2005,  1551 
  • 4 Chen XY. Bao WL. Zhang YM. Chin. Chem. Lett.  2000,  11:  483 
  • 5 Wang XX. Mao H. Yu Y. Zhu XD. Zhu CL. Synth. Commun.  2007,  37:  3751 
  • 6 Yao LB. Xu F. Shen Q. Chinese Sci. Bull.  2010,  55:  4108 
  • 7 Concellon JM. Bernad PL. Bardales E. Chem. Eur. J.  2004,  10:  2445 
  • 8 Wang XX. Zhang YM. Chin. Chem. Lett.  2004,  15:  511 
  • 9 Liu YK. Zheng H. Xu DQ. Xu ZY. Zhang YM.
    J. Zhejiang Univ. Sci. B.  2006,  7:  193 
  • 10 Fan XS. Zhang YM. Chin. Chem. Lett.  2002,  13:  285 
  • 11 Concellon JM. Huerta M. Tetrahedron Lett.  2003,  44:  1931 
  • 12 Stastna E. Cerny I. Pouzar V. Chodounska H. Steroids  2010,  75:  721