Palladium-Catalyzed Selective Aryl Ring C-H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes

被引：23

作者：

Annamalai, Pratheepkumar ^{[1
]}

Chen, Wu-Yin ^{[1
]}

Raju, Selvam ^{[1
]}

Hsu, Kou-Chi ^{[1
]}

Upadhyay, Nitinkumar Satyadev ^{[2
]}

Cheng, Chien-Hong ^{[2
]}

Chuang, Shih-Ching ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30003, Taiwan

[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 22期

关键词：

alkynes; aromatic homologation; C-H activation; naphthalenes; palladium; N BOND FORMATION; OXIDATIVE ANNULATION; ONE-POT; MOLECULAR PACKING; DIRECT ARYLATION; DIRECTING GROUP; ALKYNES; FUNCTIONALIZATION; DERIVATIVES; CLEAVAGE;

D O I：

10.1002/adsc.201600488

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho C-H bond activation/alkyne insertion/meta C-H bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1-yl) aryl] acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30-40% yield by intramolecular C-N bond formation.

引用

页码：3642 / 3648

页数：7

共 50 条

[21] Selective Diacetoxylation of Disubstituted 1,2,3-Triazoles through Palladium-Catalyzed C-H Activation
Yang, Jianhua
Zhao, Fen
Liu, Yaowen
Luo, Fang
Cheng, Huiling
Jiang, Yubo
SYNLETT, 2018, 29 (10) : 1373 - 1378
[22] Axially Chiral 2-Hydroxybiaryls by Palladium-Catalyzed Enantioselective C-H Activation
Losada, Pablo
Goicoechea, Laura
Mascarenas, Jose Luis
Gulias, Moises
ACS CATALYSIS, 2023, 13 (21) : 13994 - 13999
[23] Palladium-Catalyzed Sequential C-H Activation/Amination of 2-Iodobiphenyls with Benzoisoxazoles for Synthesis of Carbazoles
Zhao, Ya-Heng
Chen, Jun-Hua
Liu, Miao-Chang
Zhou, Yun-Bing
Wu, Hua-Yue
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 2939 - 2943
[24] Expedient Access to 2-Benzazepines by Palladium-Catalyzed C-H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold
Virelli, Matteo
Moroni, Elisabetta
Colombo, Giorgio
Fiengo, Lorenzo
Porta, Alessio
Ackermann, Lutz
Zanoni, Giuseppe
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (62) : 16516 - 16520
[25] Palladium(II)-Catalyzed Mono- and Bis-alkenylation of N-Acetyl-2-aminobiaryls through Regioselective C-H Bond Activation
Annamalai, Pratheepkumar
Hsu, Kou-Chi
Raju, Selvam
Hsiao, Huan-Chang
Chou, Chih-Wei
Lin, Gu-Ying
Hsieh, Cheng-Ming
Chen, Pei-Ling
Liu, Yi-Hung
Chuang, Shih-Ching
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) : 3840 - 3856
[26] Palladium-Catalyzed [3+2] and [2+2+2] Annulations of 4-Iodo-2-quinolones with Activated Alkynes through Selective C-H Activation
Yamamoto, Yoshihiko
Jiang, Jiyue
Yasui, Takeshi
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (17) : 3749 - 3757
[27] Synthesis of Carbazoles from 2-Iodobiphenyls by Palladium-Catalyzed C-H Activation and Amination with Diaziridinone
Shao, Changdong
Zhou, Bo
Wu, Zhuo
Ji, Xiaoming
Zhang, Yanghui
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (05) : 887 - 892
[28] Palladium-Catalyzed Annulation of Diarylamines with Olefins through C-H Activation: Direct Access to N-Arylindoles
Sharma, Upendra
Kancherla, Rajesh
Naveen, Togati
Agasti, Soumitra
Maiti, Debabrata
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) : 11895 - 11899
[29] Controlling Regioselectivity in Palladium-Catalyzed C-H Activation/Aryl-Aryl Coupling of 4-Phenylamino[2.2]paracyclophane
Zippel, Christoph
Spuling, Eduard
Hassan, Zahid
Polamo, Mika
Nieger, Martin
Braese, Stefan
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (61) : 13771 - 13775
[30] Palladium-Catalyzed Oxidative Annulation via C-H/N-H Functionalization: Access to Substituted Pyrroles
Peng, Shiyong
Wang, Lei
Huang, Jiayao
Sun, Shaofa
Guo, Haibing
Wang, Jian
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2550 - 2557

← 1 2 3 4 5 →