Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (08): 1059-1065. Previous Articles     Next Articles

Review

含硅路易斯酸的发展及其在有机合成中的应用

唐子龙1,2   

  1. (1湖南科技大学化学化工学院 湘潭 411201)
    (2 Department of Chemistery, University of Louvain, l Place Louis Pasteur B-1348 Louvain-la-neuve Belgique)
  • 收稿日期:2005-12-08 修回日期:2006-06-15 发布日期:2006-07-26
  • 通讯作者: 唐子龙

Development of Silicon-Based Lewis Acids and Their Applications to Organic Synthesis

TANG Zi-Long1,2   

  1. (1 School of Chemistry and Chemical Engineering, Hunan University of Science and Tech-nology, Xiangtan 411201)
    (2 Department of Chemistery, University of Lou-vain, 1 Place Louis Pasteur B-1348 Louvain-la-neuve Belgique)
  • Received:2005-12-08 Revised:2006-06-15 Published:2006-07-26
  • Contact: TANG Zi-Long

This paper mainly describes the development, synthesis and applications of silicon-based Lewis acids R3SiX [X=I, OTf, NTf2, C(C6F5)Tf2, etc.] and (R3SiX+MLn). They were principally used to catalyze aldol, allylation, Diels-Alder, ene and Friedel-Crafts reactions. SLAs were used in 0.5~20 mol%, and the yields of the catalyzed reactions varied from moderate to excellent with the different reactivity of silicon-based Lewis acids. The order of the reactivities is R3SiNTf2>R3SiOTf, (R3SiX+MLn)>R3SiX. The development and applications of chiral SLAs are also reviewed. When chiral trialkylsilyl bis(perfluoromethanesulfonyl)imides were used as catalysts for Diels-Alder reaction of cyclopentadiene and methyl acrylate, ee value of the reaction was up to 54%.

Key words: application, development, synthesis, (chiral) silicon-based Lewis acid