Samarium(II) iodide mediated reductions -: Influence of various additives

被引:182
作者
Dahlén, A [1 ]
Hilmersson, G [1 ]
机构
[1] Univ Gothenburg, Dept Chem, S-41296 Gothenburg, Sweden
关键词
samarium; samarium iodide; reduction; additives; co-solvent;
D O I
10.1002/ejic.200400442
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Samarium(II) iodide is a one-electron transfer reagent that has become highly appreciated as a mild and selective reducing agent in recent years. It has been found experimentally that various additives and co-solvents largely control the reactivity of SmI2. This microreview provides an overview of the current knowledge of the reagent SmI2 as a reducing agent, in particular with additives that increase its reactivity. The use of various proton sources is covered, as well as the effect of co-solvents. Furthermore, the very powerful reagent mixture SmI2/H2O/amine is also described. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
引用
收藏
页码:3393 / 3403
页数:11
相关论文
共 88 条
[1]   GENERATION AND REACTION OF SAMARIUM(II) IODIDE EQUIVALENT FROM SAMARIUM AND CHLOROTRIMETHYLSILANE SODIUM-IODIDE SYSTEM IN ACETONITRILE [J].
AKANE, N ;
KANAGAWA, Y ;
NISHIYAMA, Y ;
ISHII, Y .
CHEMISTRY LETTERS, 1992, (12) :2431-2434
[2]   SAMARIUM(II) IODIDE-HMPA - A VERY EFFICIENT SYSTEM FOR THE SELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
CABRERA, A ;
ALPER, H .
TETRAHEDRON LETTERS, 1992, 33 (35) :5007-5008
[3]   NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS [J].
CABRI, W ;
CANDIANI, I ;
COLOMBO, M ;
FRANZOI, L ;
BEDESCHI, A .
TETRAHEDRON LETTERS, 1995, 36 (06) :949-952
[4]   The role of proton donors in Sml2-mediated ketone reduction:: New mechanistic insights [J].
Chopade, PR ;
Prasad, E ;
Flowers, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :44-45
[5]   Very rapid preparation of SmI2 by sonic treatment of iodoform and metallic samarium [J].
Concellón, JM ;
Rodríguez-Solla, H ;
Bardales, E ;
Huerta, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) :1775-1778
[6]   Addition reaction of vinylic reagents, derived from α-chloroenones, to carbonyl compounds promoted by samarium diiodide [J].
Concellón, JM ;
Bernad, PL ;
Huerta, M ;
García-Granda, S ;
Díaz, MR .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (21) :5343-5347
[7]  
Concellón JM, 2002, CHEM-EUR J, V8, P4493, DOI 10.1002/1521-3765(20021004)8:19<4493::AID-CHEM4493>3.0.CO
[8]  
2-U
[9]   Microwave-assisted generation of lanthanide(II) halides in THF and simple quantitative determination [J].
Dahlen, A ;
Hilmersson, G .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (15) :3020-3024
[10]   Rapid SmI2-mediated reductions of alkyl halides and electrochemical properties of SmI2/H2O/amine [J].
Dahlén, A ;
Hilmersson, G ;
Knettle, BW ;
Flowers, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4870-4875