Highly efficient and selective trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by polystyrene-bound tin(IV) porphyrin

被引：18

作者：

Gharaati, Shadab ^{[1
,2
]}

Moghadam, Majid ^{[1
]}

Tangestaninejad, Shahram ^{[1
]}

Mirkhani, Valiollah ^{[1
]}

Mohammadpoor-Baltork, Iraj ^{[1
]}

机构：

[1] Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran

[2] Payame Noor Univ, Dept Chem, Tehran, Iran

来源：

POLYHEDRON | 2012年 / 35卷 / 01期

关键词：

Alcohol; Phenol; Trimethylsilyl ether; Polystyrene; High-valent tin(IV) porphyrin; HIGH-VALENT METALLOPORPHYRIN; ALLYL VINYL ETHERS; HYDROXYL-GROUPS; CHEMOSELECTIVE TRIMETHYLSILYLATION; PRACTICAL PROTOCOL; O-SILYLATION; SILICA-GEL; PROTECTION; EPOXIDES; HMDS;

D O I：

10.1016/j.poly.2012.01.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In the present work, investigation of the catalytic activity of tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn-IV(TNH2PP)(OTf)(2)]. supported on chloromethylated polystyrene in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV-Vis spectroscopic methods. This catalyst was used for selective trimethylsilylation of different alcohols and phenols with HMDS, with short reaction times and high yields. Also the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：87 / 95

页数：9

共 54 条

[1] ON PREPARATION OF METALLOPORPHYRINS
ADLER, AD
LONGO, FR
KAMPAS, F
KIM, J
[J]. JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1970, 32 (07): : 2443 - &
[2] 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
[3] 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
[4] 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
[5] ELECTROCHEMICAL POLYMERIZATION OF AMINO-SUBSTITUTED, PYRROLE-SUBSTITUTED, AND HYDROXY-SUBSTITUTED TETRAPHENYLPORPHYRINS
BETTELHEIM, A
WHITE, BA
RAYBUCK, SA
MURRAY, RW
[J]. INORGANIC CHEMISTRY, 1987, 26 (07) : 1009 - 1017
[6] Burgess K, 2000, SOLID-PHASE ORGANIC SYNTHESIS, P1
[7] CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99
[8] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[9] Heterogeneous catalysis in trimethylsilylation of alcohols and phenols by zirconium sulfophenyl phosphonate
Curini, M
Epifano, F
Marcotullio, MC
Rosati, O
Costantino, U
[J]. SYNTHETIC COMMUNICATIONS, 1999, 29 (03) : 541 - 546
[10] Tungstophosphoric acid (H3PW12O40) as a heterogeneous inorganic catalyst.: Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions
Firouzabadi, H
Iranpoor, N
Amani, K
Nowrouzi, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2601 - 2604

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