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Free‐Amine‐Directed Iridium‐Catalyzed C−H Bond Activation and Cyclization of Naphthalen‐1‐amines with Diazo Compounds Leading to Naphtho[1,8‐ bc ]pyridines
Author(s) -
Yan Kelu,
Lin Yongxue,
Kong Yong,
Li Bin,
Wang Baiquan
Publication year - 2019
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.201801598
Subject(s) - chemistry , diazo , iridium , imine , amine gas treating , catalysis , medicinal chemistry , pyridine , lone pair , combinatorial chemistry , stereochemistry , organic chemistry , molecule
Abstract Iridium‐catalyzed C−H activation and cyclization of naphthalen‐1‐amines with diazo compounds leading to naphtho[1,8‐ bc ]pyridines have been developed. Different from the previous free‐amine‐directed C−H functionalization with diazo compounds that relied on the coordination of lone pair electrons or in situ formation of imine, this transformation passes through a five‐membered iridacycle intermediate containing an N−Ir σ‐bond. It offers an alternative approach for the synthesis of useful diverse naphtho[1,8‐ bc ]pyridine derivatives in mild conditions.