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Palladium‐Catalyzed Selective Aryl Ring C–H Activation of N ‐Acyl‐2‐aminobiaryls: Efficient Access to Multiaryl‐Substituted Naphthalenes
Author(s) -
Annamalai Pratheepkumar,
Chen WuYin,
Raju Selvam,
Hsu KouChi,
Upadhyay Nitinkumar Satyadev,
Cheng ChienHong,
Chuang ShihChing
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600488
Subject(s) - chemistry , alkyne , intramolecular force , palladium , catalysis , aryl , yield (engineering) , ring (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , alkyl , materials science , metallurgy
Abstract 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.