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Easy Access to 1‐Amino and 1‐Carbon Substituted Isoquinolines via Cobalt‐Catalyzed CH/NO Bond Activation
Author(s) -
Muralirajan Krishnamoorthy,
Kuppusamy Ramajayam,
Prakash Sekar,
Cheng ChienHong
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.201501056
Subject(s) - chemistry , annulation , catalysis , moiety , rhodium , alkyne , medicinal chemistry , ruthenium , cobalt , aryl , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
A green atom‐economical method for the synthesis of highly functionalized 1‐amino and 1‐carbon substituted isoquinolines from the reaction of N′‐ hydroxybenzimidamides and aryl ketoximes, respectively, with alkynes via pentamethylcyclopentadienylcobalt(III)‐catalyzed CH/NO bond activation is described. The external oxidant‐free annulation reaction uses the =NOH moiety in N′‐ hydroxybenzimidamides or N ‐aromatic ketone oximes as the directing group and internal oxidant. This first row transition metal‐catalyzed annulation serves as an efficient alternative for the synthesis of isoquinolines, as water is the only by‐product and expensive noble metals such as rhodium(III), iridium(III), palladium(II), and ruthenium(II) are not required. The reaction proceeds via CH activation, alkyne insertion, reductive elimination, and NO activation.