A Mild, Simple, Efficient, and Selective Protection of Hydroxyl Groups Using Silica-Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst

被引：3

作者：

Shaterian, Hamid Reza ^{[1
]}

Doostmohammadi, Razieh ^{[1
]}

Ghashang, Majid ^{[1
]}

Rahmani, Mashaallah ^{[1
]}

机构：

[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2008年 / 183卷 / 12期

关键词：

Alcohol; heterogeneous catalyst; hexamethyldisilazane; NaHSO4-SiO2; oxime; silylation;

D O I：

10.1080/10426500802066054

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A mild, simple, novel, and highly efficient method for the rapid protection of various primary, secondary, tertiary aliphatic alcohols, aromatic alcohols, and oximes using hexamethyldisilazane (HMDS) in the presence of silica-supported sodium hydrogen sulfate (NaHSO4-SiO2), as an active, inexpensive, nontoxic, heterogeneous, and readily available catalyst under ambient conditions is described. Timethylsilyl ethers were prepared in high to excellent yields, with short reaction times under mild and almost neutral reaction conditions at room temperature.

引用

页码：3127 / 3135

页数：9

共 37 条

[1] An efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of cupric sulfate pentahydrate under neutral reaction conditions
Akhlaghinia, B
Tavakoli, S
[J]. SYNTHESIS-STUTTGART, 2005, (11): : 1775 - 1778
[2] Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispersed in silica gel under neutral condition
Azizi, N
Yousefi, R
Saidi, MR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (05) : 817 - 820
[3] Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions
Azizi, N
Saidi, MR
[J]. ORGANOMETALLICS, 2004, 23 (06) : 1457 - 1458
[4] Chemoselective silylation of alcohols
Bandgar, BP
Wadgaonkar, PP
[J]. SYNTHETIC COMMUNICATIONS, 1997, 27 (12) : 2069 - 2074
[5] Selective monoacetylation of unsymmetrical diols catalyzed by silica gel-supported sodium hydrogen sulfate
Breton, GW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) : 8952 - 8954
[6] Brook M. A, 2000, SILICON ORGANIC ORGA
[7] Chaudhury S. C., 1979, TETRAHEDRON LETT, V20, P99, DOI 10.1016/S0040-4039(01)85893-7
[8] CLARK JH, 2000, CLEAN SYNTHESIS USIN
[9] TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN
COREY, EJ
SNIDER, BB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) : 2549 - &
[10] Lewis acids:: From conventional homogeneous to green homogeneous and heterogeneous catalysis
Corma, A
García, H
[J]. CHEMICAL REVIEWS, 2003, 103 (11) : 4307 - 4365

← 1 2 3 4 →