Catalytic dihydroxylation of olefins with hydrogen peroxide: An organic-solvent- and metal-free system

被引：162

作者：

Usui, Y ^{[1
]}

Sato, K ^{[1
]}

Tanaka, M ^{[1
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, AIST, Res Inst Green Technol, Tsukuba, Ibaraki 3058565, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 45期

关键词：

alkenes; dihydroxylation; green chemistry; hydrogen peroxide; oxidation;

D O I：

10.1002/anie.200352568

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Green and convenient: Olefins are oxidized to 1,2-diols in high yield with 30% H2O2 in the presence of resin-supported sulfonic acid (see scheme) under metal-free conditions without any organic solvent. The catalyst can be recycled easily and is effective for at least 10 cycles.

引用

页码：5623 / 5625

页数：3

共 50 条

[31] Metal-free chemoselective oxidation of sulfides to sulfoxides by hydrogen peroxide catalyzed by in situ generated dodecyl hydrogen sulfate in the absence of organic co-solvents [J].

Firouzabadi, H ;

Iranpoor, N ;

Jafari, AA ;

Riazymontazer, E .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (4-5) :434-438

[32] Highly Selective Metal-Free Electrochemical Production of Hydrogen Peroxide on Functionalized Vertical Graphene Edges [J].

Zhang, Ding ;

Tsounis, Constantine ;

Ma, Zhipeng ;

Djaidiguna, Dominique ;

Bedford, Nicholas M. ;

Thomsen, Lars ;

Lu, Xunyu ;

Chu, Dewei ;

Amal, Rose ;

Han, Zhaojun .

SMALL, 2022, 18 (01)

[33] Nitrogen and sulfur doped mesoporous carbon as metal-free electrocatalysts for the in situ production of hydrogen peroxide [J].

Perazzolo, Valentina ;

Durante, Christian ;

Pilot, Roberto ;

Paduano, Andrea ;

Zheng, Jian ;

Rizzi, Gian Andrea ;

Martucci, Alessandro ;

Granozzi, Gaetano ;

Gennaro, Armando .

CARBON, 2015, 95 :949-963

[34] Metal-free carbon nitride photocatalysis with in situ hydrogen peroxide generation for the degradation of aromatic compounds [J].

Torres-Pinto, Andre ;

Sampaio, Maria J. ;

Silva, Claudia G. ;

Faria, Joaquim L. ;

Silva, Adrian M. T. .

APPLIED CATALYSIS B-ENVIRONMENTAL, 2019, 252 :128-137

[35] Cyclohexene and cycloodene epoxidation with aqueous hydrogen peroxide using transition metal-free sol-gel alumina as catalyst [J].

Rinaldi, R ;

Sepúlveda, J ;

Schuchardt, U .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :281-285

[36] Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System [J].

Rafique, Jamal ;

Saba, Sumbal ;

Rosario, Alisson R. ;

Braga, Antonio L. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (33) :11854-11862

[37] Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins [J].

Sedgwick, Daniel M. ;

Lopez, Ines ;

Roman, Raquel ;

Kobayashi, Nanako ;

Okoromoba, Otome E. ;

Xu, Bo ;

Hammond, Gerald B. ;

Barrio, Pablo ;

Fustero, Santos .

ORGANIC LETTERS, 2018, 20 (08) :2338-2341

[38] Chiral Guanidinium Ionic Liquids for Asymmetric Dihydroxylation of Olefins with Recycling of the Catalytic System by Supercritical CO2 [J].

Branco, Luis C. ;

Serbanovic, Ana ;

da Ponte, Manuel N. ;

Afonso, Carlos A. M. .

ACS CATALYSIS, 2011, 1 (10) :1408-1413

[39] An efficient organic solvent-free methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide [J].

Yamazaki, Shigekazu .

TETRAHEDRON, 2008, 64 (39) :9253-9257

[40] Converting water impurity in organic solvent into hydrogen and hydrogen peroxide by organic semiconductor photocatalyst [J].

Wu, Zhenyu ;

Wang, Xiting ;

Li, Yi ;

Zhao, Han ;

Wang, Jiawei ;

Huang, Hui ;

Liu, Yang ;

Kang, Zhenhui .

APPLIED CATALYSIS B-ENVIRONMENT AND ENERGY, 2022, 305

← 1 2 3 4 5 →