Tert-butyl nitrite: a metal-free radical initiator for aerobic cleavage of benzylic C=C bonds in compressed carbon dioxide

被引：56

作者：

Miao, Cheng-Xia ^{[1
]}

Yu, Bing

He, Liang-Nian

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

来源：

GREEN CHEMISTRY | 2011年 / 13卷 / 03期

基金：

中国国家自然科学基金;

关键词：

STEP ALKENE CLEAVAGE; CATALYTIC OXIDATIONS; HYDROGEN-PEROXIDE; OLEFINS;

D O I：

10.1039/c0gc00676a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tert-butyl nitrite easily releasing alkoxyl radical and NO in combination with compressed CO2 under metal free condition was applied to efficiently and selectively initiate aerobic cleavage of benzylic C=C bonds. Notably, compressed CO2 in this study not only provides a safe reaction environment but also tunes the selectivity.

引用

页码：541 / 544

页数：4

共 28 条

[11]

Larock R.C., 1999, COMPREHENSIVE ORGANI, V2nd, P1213

[12] Optimization of a biocatalytic single-step alkene cleavage of aryl alkenes [J].

Mang, Harald ;

Gross, Johannes ;

Lara, Miguel ;

Goessler, Christian ;

Schoemaker, Hans E. ;

Guebitz, Georg M. ;

Kroutil, Wolfgang .

TETRAHEDRON, 2007, 63 (16) :3350-3354

[13] Biocatalytic single-step alkene cleavage from aryl alkenes: An enzymatic equivalent to reductive ozonization [J].

Mang, Harald ;

Gross, Johannes ;

Lara, Miguel ;

Goessler, Christian ;

Schoemaker, Hans E. ;

Guebitz, Georg M. ;

Kroutil, Wolfgang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) :5201-5203

[14] Catalytic oxidations in carbon dioxide-based reaction media, including novel CO2-expanded phases [J].

Musie, G ;

Wei, M ;

Subramaniam, B ;

Busch, DH .

COORDINATION CHEMISTRY REVIEWS, 2001, 219 :789-820

[15] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].

PAPPO, R ;

ALLEN, DS ;

LEMIEUX, RU ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479

[16] Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer -: A biomimetic approach [J].

Piera, Julio ;

Backvall, Jan-E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3506-3523

[17] Transformation of carbon dioxide [J].

Sakakura, Toshiyasu ;

Choi, Jun-Chul ;

Yasuda, Hiroyuki .

CHEMICAL REVIEWS, 2007, 107 (06) :2365-2387

[18] Catalytic Oxidations in Dense Carbon Dioxide [J].

Seki, Tsunetake ;

Baiker, Alfons .

CHEMICAL REVIEWS, 2009, 109 (06) :2409-2454

[19] Catalytic oxidations mediated by metal ions and nitroxyl radicals [J].

Sheldon, Roger A. ;

Arends, Isabel W. C. E. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 251 (1-2) :200-214

[20]

Shing T.K. M., 1991, Comprehensive Organic Synthesis, V7, P703

← 1 2 3 →