Rhodium(III)-Catalyzed Divergent C-H Functionalization of N-Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts

被引：16

作者：

Ren, Jie

Yang, Liu

Pi, Chao

Cui, Xiuling ^{[1
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Green Catalysis Ctr, Key Lab Appl Chem Henan Univ, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 11期

关键词：

C-H bond functionalization; Hypervalent iodine-(III) ylides; Intramolecular proton transfer; Carbazolones; Zwitterionic salts; RAPID ACCESS; ACTIVATION; PHENOXYACETAMIDES; ANNULATION; RH(III); INDOLE; BOND;

D O I：

10.1002/adsc.202201390

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We described an Rhodium(III)-catalyzed divergent C-H bond functionalization of N-aryl amidines with iodonium ylides. Carbazolones and zwitterionic salts were diversely constructed through intermolecular annulation and intramolecular proton transfer under the different reaction conditions. This protocol is operationally simple and tolerates a variety of functional groups. The efficient post-modification of pharmaceutical molecules demonstrates its practicability.

引用

页码：1817 / 1823

页数：7

共 50 条

[31] Rhodium(III)-catalyzed chemoselective C-H functionalization of benzamides with methyleneoxetanones controlled by the solvent
Bian, Mengyao
Ma, Kuangshun
Mawjuda, Hamdulla
Yu, Xiyong
Li, Xingwei
Gao, Hui
Zhou, Zhi
Yi, Wei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) : 6114 - 6118
[32] Rhodium(III)-Catalyzed Indazole Synthesis by C-H Bond Functionalization and Cyclative Capture
Lian, Yajing
Bergman, Robert G.
Lavis, Luke D.
Ellman, Jonathan A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) : 7122 - 7125
[33] Rhodium(III)-Catalyzed C-H Vinylation of Arenes: Access to Functionalized Styrenes
Zhou, Jun
Li, Xin
Liao, Gang
Shi, Bing-Feng
CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) : 1143 - 1146
[34] Rhodium(III)-Catalyzed Atroposelective C-H Indolylization of 1-Aryl Isoquinolines with 3-Indolylphenyliodonium Salts
Zheng, Dong-Song
Zheng, Jun
Wang, Qiang
Gu, Qing
You, Shu-Li
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (20) : 2684 - 2690
[35] Rh(III)-Catalyzed Aldehydic C-H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
Xu, Guo-Dong
Huang, Kenneth L.
Huang, Zhi-Zhen
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (14) : 3318 - 3323
[36] Rhodium(III)-catalyzed chemodivergent annulations between N-methoxybenzamides and sulfoxonium ylides via C-H activation
Xu, Youwei
Zheng, Guangfan
Yang, Xifa
Li, Xingwei
CHEMICAL COMMUNICATIONS, 2018, 54 (06) : 670 - 673
[37] Rhodium(III)-Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C-H Bond Activation
Meng, Yan-Yu
Zhu, Wen-Jing
Song, Yuan-Yuan
Bu, Gang-Gang
Zhang, Li-Juan
Xu, Fen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1290 - 1294
[38] Catalyst and solvent switched divergent C-H functionalization: oxidative annulation of N-aryl substituted quinazolin-4-amine with alkynes
Meesa, Siddi Ramulu
Naikawadi, Praveen Kumar
Gugutothu, Kishan
Kumar, K. Shiva
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (16) : 3032 - 3037
[39] Aryl Triflates in Phosphorus-Directed Rhodium(III)-Catalyzed C-H Activation
Roger, Julien
Sire, Charline
Tsivery, Anthonia
Cattey, Helene
Hierso, Jean-Cyrille
SYNTHESIS-STUTTGART, 2023, 55 (21): : 3589 - 3599
[40] Synthesis of CF3-substituted isoindolones via rhodium(III)-catalyzed carbenoid C-H functionalization of aryl hydroxamates
Vorobyeva, Daria V.
Bubnova, Alexandra S.
Buyanovskaya, Anastasiya G.
Osipov, Sergey N.
MENDELEEV COMMUNICATIONS, 2023, 33 (01) : 34 - 36

← 1 2 3 4 5 →