Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies

被引:24
作者
Bartoszewicz, Agnieszka [1 ]
Kalek, Marcin [1 ]
Stawinski, Jacek [1 ,2 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
[2] Polish Acad Sci, Inst Bioorgan Chem, PL-61704 Poznan, Poland
基金
瑞典研究理事会;
关键词
D O I
10.1016/j.tet.2008.06.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient silylating system for 1 degrees, 2 degrees, and 3 degrees, alcohols, consisting of a silyl chloride/N-methylimidazole/iodine, was developed. Synthetic and mechanistic aspects of this new reagent system, and particularly the role of iodine were investigated in detail using H-1 NMR spectroscopy. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8843 / 8850
页数:8
相关论文
共 28 条
[1]  
AIZPURUA JM, 1985, TETRAHEDRON LETT, V26, P275
[2]   ON THE HYDROLYSIS OF TRIALKYLPHENOXYSILANES .2. [J].
AKERMAN, E .
ACTA CHEMICA SCANDINAVICA, 1957, 11 (02) :373-381
[3]   FACILE SYNTHESIS OF 4-SUBSTITUTED PYRIDINES USING GRIGNARD-REAGENTS [J].
AKIBA, K ;
ISEKI, Y ;
WADA, M .
TETRAHEDRON LETTERS, 1982, 23 (38) :3935-3936
[4]   STERICALLY HINDERED SILYL PERCHLORATES AS BLOCKING REAGENTS [J].
BARTON, TJ ;
TULLY, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3649-3653
[5]   A new reagent system for efficient silylation of alcohols:: Silyl chloride-N-methylimidazole-iodine [J].
Bartoszewicz, Agnieszka ;
Kalek, Marcin ;
Nilsson, Johan ;
Hiresova, Renata ;
Stawinski, Jacek .
SYNLETT, 2008, (01) :37-40
[6]  
CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99
[7]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[8]   Supersilylating agents from chlorosilanes [J].
Davis, AP ;
Muir, JE ;
Plunkett, SJ .
TETRAHEDRON LETTERS, 1996, 37 (52) :9401-9402
[9]   A high yielding preparation of α-trimethylsilyloxyphosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine [J].
Firouzabadi, H ;
Iranpoor, N ;
Sobhani, S .
TETRAHEDRON LETTERS, 2002, 43 (20) :3653-3655
[10]  
GREENWOOD NN, 1984, CHEM ELEMENTS, P978