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Rh III ‐Catalyzed CH Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts
Author(s) -
Luo ChingZong,
Gandeepan Parthasarathy,
Jayakumar Jayachandran,
Parthasarathy Kanniyappan,
Chang YuWei,
Cheng ChienHong
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302290
Subject(s) - pyridinium , chemistry , alkyne , rhodium , catalysis , aryl , annulation , pyridine , medicinal chemistry , reductive elimination , reaction mechanism , substrate (aquarium) , combinatorial chemistry , stereochemistry , organic chemistry , alkyl , oceanography , geology
An efficient and convenient method for the synthesis of highly substituted polycyclic pyridinium salts from the reaction of various 2‐aryl‐pyridines and 2‐aryl‐sp 2 ‐nitrogen‐atom‐containing heterocycles with alkynes through rhodium(III)‐catalyzed CH activation and annulation under an O 2 atmosphere is described. A possible mechanism that involves the chelation‐assisted CH activation of the 2‐aryl‐pyridine substrate, insertion of the alkyne, and reductive elimination is proposed. This mechanism was supported by the isolation of a five‐membered rhodacycle ( I′ ). In addition, kinetic isotope studies were performed to understand the intimate reaction mechanism.