Efficient synthesis of carbonyl compounds: oxidation of azides and alcohols catalyzed by vanadium pentoxide in water using tert-butylhydroperoxide

被引：58

作者：

Alagiri, Kaliyamoorthy ^{[1
]}

Prabhu, Kandikere Ramaiah ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON | 2011年 / 67卷 / 44期

关键词：

Oxidation; tert-Butylhydroperoxide; Azides; Alcohols; Carbonyl compounds; HIGHLY SELECTIVE OXIDATION; ASYMMETRIC EPOXIDATION; AEROBIC OXIDATION; CARBOXYLIC-ACIDS; COORDINATION CHEMISTRY; RADICAL AZIDONATION; MOLYBDENUM XANTHATE; SECONDARY ALCOHOLS; MOLECULAR-OXYGEN; ALLYLIC ALCOHOLS;

D O I：

10.1016/j.tet.2011.08.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic amount of vanadium reagent with tert-butylhydroperoxide as the oxidant was found to be an excellent oxidizing agent in aqueous medium. Vanadium pentoxide with aq tert-butylhydroperoxide readily oxidizes primary benzylic azides to the corresponding acids and secondary benzylic azides to the corresponding ketones in excellent yields. Further, vanadium pentoxide and aq tert-butylhydroperoxide combination turned out to be an effective catalyst for the oxidation of alcohols. Using vanadium pentoxide and aq tert-butylhydroperoxide primary alcohols were oxidized to the corresponding acids, whereas secondary alcohols underwent a smooth transformation to furnish corresponding ketones in excellent yields. All the oxidations are performed in water. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：8544 / 8551

页数：8

共 90 条

[1] Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst [J].