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

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• 作者：Pratheepkumar Annamalai ; Wu-Yin Chen ; Selvam Raju ; Kou-Chi Hsu ; Nitinkumar Satyadev Upadhyay ; Chien-Hong Cheng and Shih-Ching Chuang
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：November 17, 2016
• 年：2016
• 卷：358
• 期：22
• 页码：3642-3648
• 全文大小：1398K
• ISSN：1615-4169

文摘

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.