Oxidation of C-H bonds to C=O bonds by O2 only or N-oxides and DMSO: synthesis of Δ1-bipyrrolinones and pyrrolino[3,2-b]pyrrolinones from 2,6-diazasemibullvalenes

被引：11

作者：

Zhang, Shaoguang ^{[1
]}

Zhan, Ming ^{[1
]}

Luo, Qian ^{[1
]}

Zhang, Wen-Xiong ^{[1
]}

Xi, Zhenfeng ^{[1
,2
]}

机构：

[1] Peking Univ, Coll Chem, Beijing Natl Lab Mol Sci, MOE Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[2] Chinese Acad Sci, SIOC, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 55期

关键词：

MOLECULAR-OXYGEN; SINGLET OXYGEN; AZIRIDINES; DIMETHOXYCARBENE; DERIVATIVES; EFFICIENT; CHEMISTRY; CARBONYL; KETONES;

D O I：

10.1039/c3cc43061h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,6-Diazasemibullvalenes (NSBVs) readily reacted with oxygen under mild conditions, affording Delta(1)-bipyrrolinones via C-N bond cleavage and C-H bond oxidation. Pyrrolino[3,2-b]pyrrolinone derivatives were efficiently generated when NSBVs were treated with N-oxides in the presence of Lewis acids. Delta(1)-Bipyrrolinones thus obtained could be readily transformed into other heterocycles.

引用

页码：6146 / 6148

页数：3

共 26 条

[1] Plasmonic O2 dissociation and spillover expedite selective oxidation of primary C-H bonds
Li, Hao
Shang, Huan
Jiang, Fuze
Zhu, Xingzhong
Ruan, Qifeng
Zhang, Lizhi
Wang, Jing
CHEMICAL SCIENCE, 2021, 12 (46) : 15308 - 15317
[2] Selective Solvent-Free and Additive-Free Oxidation of Primary Benzylic C-H Bonds with O2 Catalyzed by the Combination of Metalloporphyrin with N-Hydroxyphthalimide
Shen, Hai-Min
Qi, Bei
Hu, Meng-Yun
Liu, Lei
Ye, Hong-Liang
She, Yuan-Bin
CATALYSIS LETTERS, 2020, 150 (11) : 3096 - 3111
[3] Efficient and selective oxidation of tertiary benzylic C-H bonds with O2 catalyzed by metalloporphyrins under mild and solvent-free conditions
Shen, Hai-Min
Hu, Meng-Yun
Liu, Lei
Qi, Bei
Ye, Hong-Liang
She, Yuan-Bin
APPLIED CATALYSIS A-GENERAL, 2020, 599
[4] Activation of C(SP3)-H Bonds Promoted Oxidation of Sulfides by O2 Under Catalyst-Free Conditions
Wang, Zufeng
Wang, Hongyi
Zhao, Zhiying
Zhu, Yu
Deng, Youer
Li, Xiaolong
Zeng, Dan
Liu, Yachun
Zhang, Chao
Fu, Zaihui
JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2024, 46 (03): : 300 - 308
[5] 1-(2-Aminophenyl)-3-(4-pyridyl)prop-2-en-1-one: a three-dimensional framework structure built from N-H•••N, C-H•••O and C-H•••π(arene) hydrogen bonds
Cuenu, Fernando
Abonia, Rodrigo
Cobo, Justo
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2010, 66 : O589 - O592
[6] (2R*,4S*)-2-(Pyridin-3-yl)-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol: a three-dimensional framework built from O-H•••N, C-H•••O and C-H•••π(arene) hydrogen bonds
Gomez, Sandra L.
Palma, Alirio
Cobo, Justo
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2011, 67 : O157 - O160
[7] Efficient and selective oxidation of secondary benzylic C-H bonds to ketones with O2 catalyzed by metalloporphyrins under solvent-free and additive-free conditions
Shen, Hai-Min
Liu, Lei
Qi, Bei
Hu, Meng-Yun
Ye, Hong-Liang
She, Yuan-Bin
MOLECULAR CATALYSIS, 2020, 493
[8] Octyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate: complex sheets built from N-H•••N, C-H•••N and C-H•••O hydrogen bonds
Cortes, Edwar
Abonia, Rodrigo
Cobo, Justo
Glidewell, Christopher
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2014, 70 : 617 - +
[9] (NH4)4[NiMo6O24H6]•5H2O/g-C3N4 materials for selective photo-oxidation of C-O and C=C bonds
Caudillo-Flores, Uriel
Ansari, Fahimeh
Bachiller-Baeza, Belen
Colon, Gerardo
Fernandez-Garcia, Marcos
Kubacka, Anna
APPLIED CATALYSIS B-ENVIRONMENTAL, 2020, 278 (278)
[10] Selective Solvent-Free and Additive-Free Oxidation of Primary Benzylic C–H Bonds with O2 Catalyzed by the Combination of Metalloporphyrin with N-Hydroxyphthalimide
Hai-Min Shen
Bei Qi
Meng-Yun Hu
Lei Liu
Hong-Liang Ye
Yuan-Bin She
Catalysis Letters, 2020, 150 : 3096 - 3111

← 1 2 3 →