Highly efficient tetrahydropyranylation of alcohols and phenols catalyzed by a new and reusable high-valent vanadium(IV) porphyrin

被引：12

作者：

Taghavi, S. Abdolmanaf ^{[1
]}

Moghadam, Majid ^{[1
]}

Mohammadpoor-Baltork, Iraj ^{[1
]}

Tangestaninejad, Shahram ^{[1
]}

Mirkhani, Valiollah ^{[1
]}

Khosropour, Ahmad Reza ^{[1
]}

机构：

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

来源：

COMPTES RENDUS CHIMIE | 2011年 / 14卷 / 12期

关键词：

Vanadium porphyrin; Electron-deficient; Alcohols; Phenols; THP ether; ALLYL VINYL ETHERS; SELECTIVE TETRAHYDROPYRANYLATION; CHEMOSELECTIVE TETRAHYDROPYRANYLATION; METALLOPORPHYRIN COMPLEX; ALUMINUM-CHLORIDE; TIN(IV) PORPHYRIN; MILD; EPOXIDES; REARRANGEMENT; PROTECTION;

D O I：

10.1016/j.crci.2011.09.009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the present work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V-IV(TPP)(OTf)(2)], in the tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) is reported. This new electron-deficient V(IV) compound was used as a highly efficient catalyst for pyranylation of primary (aliphatic and benzylic), sterically-hindered secondary and tertiary alcohols with DHP. Tetrahydropyranylation of phenols with DHP was also performed to afford the desired THP-ethers. The chemoselectivity of this method was also investigated. The results indicated that primary alcohols are more reactive in the presence of secondary and tertiary alcohols and phenols. This catalyst was reused several times without loss of its activity. (C) 2011 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：1095 / 1102

页数：8

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