Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C-H activation

被引：11
作者：
Wen, Jing [1 ]
Wu, An [2 ]
Chen, Pei [1 ]
Zhu, Jin [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Nanjing 210093, Jiangsu, Peoples R China
[2] Nanjing Univ, Kuang Yaming Honors Sch, Nanjing 210093, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 38期
基金：
中国国家自然科学基金;
关键词：
Rhodium; Anilides; Internal oxidation; Alkenes; C-H activation; BOND ACTIVATION; DIRECTING GROUP; ORTHO-ARYLATION; ANILIDES; INDOLES; ARENES; AMIDATION; ALKYNES; FUNCTIONALIZATION; CYCLIZATION;
D O I：
10.1016/j.tetlet.2015.07.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Described herein is an efficient new method for ortho-olefination of anilides in the presence of AgSbF6 and NaOAc via rhodium(III)-catalyzed internal oxidative C-H bond activation based on hydroxyl as directing and oxidative group. A range of alkenes and functional groups on acetanilides is supported and a possible mechanism is proposed according to the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5282 / 5286
页数：5
相关论文
共 50 条
[41]   Rhodium-catalyzed regioselective direct C-H arylation of indoles with aryl boronic acids [J].
Wang, Liang ;
Qu, Xing ;
Li, Zhan ;
Peng, Wang-Ming .
TETRAHEDRON LETTERS, 2015, 56 (24) :3754-3757
[42]   Efficient synthesis of anthranilic esters via Pd-catalyzed dehydrogenative/decarbonylative coupling of anilides and glyoxylates [J].
Wang, Sizhuo ;
Yang, Zhiyong ;
Liu, Jidan ;
Xie, Kai ;
Wang, Anwei ;
Chen, Xiang ;
Tan, Ze .
CHEMICAL COMMUNICATIONS, 2012, 48 (79) :9924-9926
[43]   Room-Temperature Stille Coupling of Tetraarylstannanes via Palladium-Catalyzed C-H Activation [J].
Xue, Dong ;
Li, Jing ;
Liu, Yu-Xia ;
Han, Wen-Yong ;
Zhang, Zun-Ting ;
Wang, Chao ;
Xiao, Jianliang .
SYNLETT, 2012, (13) :1941-1946
[44]   Palladium-catalyzed C-H activation of anilides at room temperature: ortho-arylation and acetoxylation [J].
Yang, Fan ;
Song, Feijie ;
Li, Wei ;
Lan, Jingbo ;
You, Jingsong .
RSC ADVANCES, 2013, 3 (25) :9649-9652
[45]   Rhodium-Catalyzed Directed Sulfenylation of Arene C-H Bonds [J].
Yang, Yaxi ;
Hou, Wei ;
Qin, Lihuai ;
Du, Juanjuan ;
Feng, Huijin ;
Zhou, Bing ;
Li, Yuanchao .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) :416-420
[46]   1,2,3-Triazoles as versatile directing group for selective sp2 and sp3 C-H activation: cyclization vs substitution [J].
Ye, Xiaohan ;
He, Zhengrong ;
Ahmed, Tonia ;
Weise, Keith ;
Akhmedov, Novruz G. ;
Petersen, Jeffrey L. ;
Shi, Xiaodong .
CHEMICAL SCIENCE, 2013, 4 (09) :3712-3716
[47]   Rhodium(III)-Catalyzed C-H Activation and Amidation of Arenes Using N-Arenesulfonated Imides as Amidating Reagents [J].
Yu, Songjie ;
Wan, Boshun ;
Li, Xingwei .
ORGANIC LETTERS, 2013, 15 (14) :3706-3709
[48]   Rh-Catalyzed oxidative C-H activation/annulation: converting anilines to indoles using molecular oxygen as the sole oxidant [J].
Zhang, Guoying ;
Yu, Hui ;
Qin, Guiping ;
Huang, Hanmin .
CHEMICAL COMMUNICATIONS, 2014, 50 (33) :4331-4334
[49]   Rh(III)-Catalyzed C-H Amidation with N-Hydroxycarbamates: A New Entry to N-Carbamate-Protected Arylamines [J].
Zhou, Bing ;
Du, Juanjuan ;
Yang, Yaxi ;
Feng, Huijin ;
Li, Yuanchao .
ORGANIC LETTERS, 2014, 16 (02) :592-595
[50]   Rhodium(III)-Catalyzed Oxidative Olefination of Pyridines and Quinolines: Multigram-Scale Synthesis of Naphthyridinones [J].
Zhou, Jun ;
Li, Bo ;
Hu, Fang ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2013, 15 (13) :3460-3463
12345