Rhodium(III)-catalyzed coupling of aromatic ketazines or oximes with 2-vinyloxirane via C-H activation

被引：17

作者：

Wen, Jing ^{[1
]}

Wu, An ^{[2
]}

Miao, Yuqin ^{[1
]}

Zhu, Jin ^{[1
]}

机构：

[1] Nanjing Univ, Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem, Sch Chem & Chem Engn,Dept Polymer Sci & Engn, 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 / 41期

基金：

中国国家自然科学基金;

关键词：

Rhodium; Ketazines; Oximes; 2-Vinyloxirane; Methyl acrylate; C-H activation; BOND ACTIVATION; REGIOSPECIFIC SYNTHESIS; ARENES; CYCLIZATION; DERIVATIVES; AMIDATION; MILD; HYDROAMINATION; HETEROCYCLES; OLEFINATION;

D O I：

10.1016/j.tetlet.2015.08.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described herein is a rhodium(III)-catalyzed coupling of aromatic ketazines or oximes with 2-vinyloxirane via directed C-H activation. This reaction proceeds efficiently under mild conditions with a low catalyst loading, especially in conditions with room temperature in the absence of additives for aromatic ketazines. A wide range of substituted substrates is supported and a possible mechanism is proposed according to the experimental results of kinetic isotopic effect, reversibility studies, and catalysis with rhodacycle intermediate c1. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5512 / 5516

页数：5

共 50 条

[1] Cobalt(III)-Catalyzed C-C Coupling of Arenes with 7-Oxabenzonorbornadiene and 2-Vinyloxirane via C-H Activation
Kong, Lingheng
Yu, Songjie
Tang, Guodong
Wang, He
Zhou, Xukai
Li, Xingwei
[J]. ORGANIC LETTERS, 2016, 18 (15) : 3802 - 3805
[2] Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation
Zhou, Zhi
Liu, Guixia
Lu, Xiyan
[J]. ORGANIC LETTERS, 2016, 18 (21) : 5668 - 5671
[3] Rhodium(III)-Catalyzed Coupling of Arenes with Cyclopropanols via C-H Activation and Ring Opening
Zhou, Xukai
Yu, Songjie
Kong, Lingheng
Li, Xingwei
[J]. ACS CATALYSIS, 2016, 6 (02): : 647 - 651
[4] Rhodium(III)-Catalyzed C-H Activation of Nitrones and Annulative Coupling with Nitroalkenes
Bai, Dachang
Jia, Qingqian
Xu, Teng
Zhang, Qiuqiu
Wu, Fen
Ma, Chaorui
Liu, Bingxian
Chang, Junbiao
Li, Xingwei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9877 - 9884
[5] Rhodium(III)-Catalyzed Directed ortho-C-H Bond Functionalization of Aromatic Ketazines via C-S and C-C Coupling
Wen, Jing
Wu, An
Wang, Mingyang
Zhu, Jin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 10457 - 10463
[6] Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C-H activation
Zheng, Guangfan
Tian, Miaomiao
Xu, Youwei
Chen, Xiaohong
Li, Xingwei
[J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 998 - 1002
[7] Rhodium(III)-catalyzed synthesis of indanones via C-H activation of phenacyl phosphoniums and coupling with olefins
Li, Yunyun
Yang, Xifa
Kong, Lingheng
Li, Xingwei
[J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2114 - 2118
[8] Rhodium(iii)-catalyzed oxidative cross-coupling of benzoxazinones with styrenes via C-H activation
Yang, Xifa
Li, Song
He, Yuhao
Dai, Danhua
Bao, Mengyao
Luo, Ziyang
Liu, Xiangyang
Geng, Yuehua
Fan, Liangxin
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (04) : 797 - 806
[9] A rhodium(III)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C-H activation
Liu, Ruixing
Wei, Yin
Shi, Min
[J]. CHEMICAL COMMUNICATIONS, 2019, 55 (52) : 7558 - 7561
[10] Synthesis of 2-Substituted Quinolines via Rhodium(III)-Catalyzed C-H Activation of Imidamides and Coupling with Cyclopropanols
Zhou, Xukai
Qi, Zisong
Yu, Songjie
Kong, Lingheng
Li, Yang
Tian, Wan-Fa
Li, Xingwei
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1620 - 1625

← 1 2 3 4 5 →