Anilinosilanes/TBAF catalyst: Mild and powerful agent for the silylation of sterically hindered alcohols

被引：33

作者：

Iida, A ^{[1
]}

Horii, A ^{[1
]}

Misaki, T ^{[1
]}

Tanabe, Y ^{[1
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Sanda, Hyougo 6691337, Japan

来源：

SYNTHESIS-STUTTGART | 2005年 / 16期

关键词：

alcohols; silylation; anilinosilane; TBAF; catalyst;

D O I：

10.1055/s-2005-872098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed an efficient method for the silylation of alcohols using anilinosilane with tetrabutylaminonium fluoride (TBAF) catalyst, wherein TMS, TES and TBS groups were smoothly introduced into silylation-resistant hindered alcohols under mild conditions.

引用

页码：2677 / 2682

页数：6

共 35 条

[1] SUBSTITUTION OF 1-HALO-1-ALKYNES BY ORGANOMETALLIC DERIVATIVES OF COPPER - SYNTHESIS OF NEW CLASS OF SYNTHONS - APPLICATION TO SYNTHESIS OF BOMBYKOL [J].

COMMERCON, A ;

NORMANT, JF ;

VILLIERAS, J .

TETRAHEDRON, 1980, 36 (09) :1215-1221

[2]

COOMBES RCD, 1993, Patent No. 9312137

[3]

CORRIU RJP, 1989, CHEM ORGANIC SILICON, P1241

[4] ORGANIC-REACTIONS AT HIGH-PRESSURE - A MILD METHOD FOR THE PLACEMENT OF PROTECTING GROUPS ON HINDERED AND SENSITIVE ALCOHOLS [J].

DAUBEN, WG ;

BUNCE, RA ;

GERDES, JM ;

HENEGAR, KE ;

CUNNINGHAM, AF ;

OTTOBONI, TB .

TETRAHEDRON LETTERS, 1983, 24 (51) :5709-5712

[5] SILYL HALIDES FROM (PHENYLSELENO)SILANES - REACTION WITH OXIRANES AND ALCOHOLS TO GIVE HYDROLYTICALLY STABLE SILYL ETHERS [J].

DETTY, MR ;

SEIDLER, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1283-1292

[6] MASS SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS .155. ELECTRON IMPACT INDUCED FRAGMENTATIONS AND REARRANGEMENTS OF SOME TRIMETHYLSILYL ETHERS OF ALIPHATIC GLYCOLS AND RELATED COMPUNDS [J].

DIEKMAN, J ;

THOMSON, JB ;

DJERASSI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2271-&

[7] RHODIUM(II) PERFLUOROBUTYRATE CATALYZED SILANE ALCOHOLYSIS - A HIGHLY SELECTIVE ROUTE TO SILYL ETHERS [J].

DOYLE, MP ;

HIGH, KG ;

BAGHERI, V ;

PIETERS, RJ ;

LEWIS, PJ ;

PEARSON, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6082-6086

[8]

Greene T. W., 1999, PROTECTIVE GROUPS OR, P113

[9] HIGHLY SELECTIVE CROSS-COUPLING REACTION OF ORGANOSILICON COMPOUNDS MEDIATED BY FLUORIDE-ION AND PD CATALYST [J].

HATANAKA, Y ;

HIYAMA, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1990, 48 (09) :834-843

[10] One-step conversion of formate esters to O-silyl ethers by means of samarium diiodide in the presence of chlorosilane reagents [J].

Honda, T ;

Ishikawa, F .

SYNTHETIC COMMUNICATIONS, 1999, 29 (19) :3323-3328

← 1 2 3 4 →