Oxidative cleavage of benzylic C-N bonds under metal-free conditions

被引:29
作者
Gong, Jin-Long [1 ]
Qi, Xinxin [1 ]
Wei, Duo [1 ]
Feng, Jian-Bo [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
ZINC-CATALYZED OXIDATION; ALLYLIC SULFONYLATION; ALCOHOLS; ALDEHYDES; ESTERIFICATION; BENZAMIDES; AMIDATION; SULFONYLHYDRAZIDES; C3-FORMYLATION; AMINATION;
D O I
10.1039/c4ob01633e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An interesting procedure for the oxidative cleavage of benzylic C-N bonds has been developed. Using TBAI as the catalyst and H2O2 as the oxidant, various benzylamines were transformed into their corresponding aromatic aldehydes in moderate to good yields. Notably, this is the first example of an oxidative cleavage of benzylic C-N bonds under metal-free conditions.
引用
收藏
页码:7486 / 7488
页数:3
相关论文
共 48 条
[1]   Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584
[2]   The Copper-Catalyzed C-3-Formylation of Indole C-H Bonds using Tertiary Amines and Molecular Oxygen [J].
Chen, Jianbin ;
Liu, Bin ;
Liu, Dongfang ;
Liu, Shan ;
Cheng, Jiang .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2438-2442
[3]   Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].
Chen, Long ;
Shi, Erbo ;
Liu, Zhaojun ;
Chen, Shulin ;
Wei, Wei ;
Li, Hong ;
Xu, Kai ;
Wan, Xiaobing .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089
[4]  
Dixneuf P.H., 2013, Metal-Catalyzed Reactions in Water
[5]   Oxidative synthesis of benzamides from toluenes and DMF [J].
Feng, Jian-Bo ;
Wei, Duo ;
Gong, Jin-Long ;
Qi, Xinxin ;
Wu, Xiao-Feng .
TETRAHEDRON LETTERS, 2014, 55 (36) :5082-5084
[6]   The first zinc-catalyzed oxidation of sulfides to sulfones using H2O2 as green oxidant [J].
Feng, Jian-Bo ;
Gong, Jin-Long ;
Wu, Xiao-Feng .
RSC ADVANCES, 2014, 4 (55) :29273-29275
[7]   Calcium and magnesium chlorides-catalyzed oxidative esterification of aromatic aldehydes [J].
Feng, Jian-Bo ;
Gong, Jin-Long ;
Li, Qin ;
Wu, Xiao-Feng .
TETRAHEDRON LETTERS, 2014, 55 (09) :1657-1659
[8]   A Metal-Free Oxidative Esterification of the Benzyl C?H Bond [J].
Feng, Jie ;
Liang, Shuai ;
Chen, Shan-Yong ;
Zhang, Ji ;
Fu, Song-Sen ;
Yu, Xiao-Qi .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (07) :1287-1292
[9]   KI-catalyzed arylation of benzothiazoles from the coupling of aryl aldehydes with benzothiazoles in neat water [J].
Gao, Yuyu ;
Song, Qiuling ;
Cheng, Guolin ;
Cui, Xiuling .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (07) :1044-1047
[10]   Copper-Catalyzed Oxidative Amination of Benzoxazoles via C-H and C-N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources [J].
Guo, Shengmei ;
Chan, Bo ;
Xie, Yinjun ;
Xia, Chungu ;
Huang, Hanmin .
ORGANIC LETTERS, 2011, 13 (03) :522-525