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

被引：25

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.

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收藏

页码：3642 / 3648

页数：7

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