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
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
收藏
页码:541 / 544
页数:4
相关论文
共 28 条
[1]   Utilisation of CO2 as a chemical feedstock:: opportunities and challenges [J].
Aresta, Michele ;
Dibenedetto, Angela .
DALTON TRANSACTIONS, 2007, (28) :2975-2992
[2]   THE REACTIONS OF OZONE WITH ORGANIC COMPOUNDS [J].
BAILEY, PS .
CHEMICAL REVIEWS, 1958, 58 (05) :925-1010
[3]   THE REACTION OF NITRIC OXIDE WITH ISOBUTYLENE [J].
BROWN, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2480-2488
[4]   MECHANISM OF OZONOLYSIS [J].
CRIEGEE, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (11) :745-752
[5]   Selective aerobic oxidation of styrene to benzaldehyde catalyzed by water-soluble palladium(II) complex in water [J].
Feng, Bo ;
Hou, Zhenshan ;
Wang, Xiangrui ;
Hu, Yu ;
Li, Huan ;
Qiao, Yunxiang .
GREEN CHEMISTRY, 2009, 11 (09) :1446-1452
[6]   The barton reaction: Can a more tenable pathway be hypothesized for the formation of nitrosoalkyl derivatives? [J].
Grossi, L .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (18) :5419-5425
[7]   Organic Radical Reactions Associated with Nitrogen Monoxide [J].
Hartung, Jens .
CHEMICAL REVIEWS, 2009, 109 (09) :4500-4517
[8]   A new route to lactam precursors from cycloalkanes:: Direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide [J].
Hirabayashi, T ;
Sakaguchi, S ;
Ishii, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1120-1123
[9]   Aerobic photo-oxidative cleavage of the C-C double bonds of styrenes [J].
Hirashima, Shin-ichi ;
Kudo, Yasuhisa ;
Nobuta, Tomoya ;
Tada, Norihiro ;
Itoh, Akichika .
TETRAHEDRON LETTERS, 2009, 50 (30) :4328-4330
[10]   Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2]2+ (dmp=2,9-dimethylphenanthroline) [J].
Kogan, V ;
Quintal, MM ;
Neumann, R .
ORGANIC LETTERS, 2005, 7 (22) :5039-5042