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Heterogeneous Cu II ‐Catalysed Solvent‐Controlled Selective N‐Arylation of Cyclic Amides and Amines with Bromo‐iodoarenes
Author(s) -
Kundu Debasish,
Bhadra Sukalyan,
Mukherjee Nirmalya,
Sreedhar Bojja,
Ranu Brindaban C.
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.201302645
Subject(s) - electron paramagnetic resonance , chemistry , x ray photoelectron spectroscopy , catalysis , moiety , amide , amine gas treating , solvent , mass spectrometry , spectroscopy , nuclear magnetic resonance spectroscopy , nuclear chemistry , polymer chemistry , organic chemistry , nuclear magnetic resonance , chromatography , physics , quantum mechanics
A selective N‐arylation of cyclic amides and amines in DMF and water, respectively, catalysed by Cu II /Al 2 O 3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X‐ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma‐mass spectrometry (ICP‐MS) studies of the catalyst at different stages of the reaction. The Cu II /Al 2 O 3 catalyst was recovered and recycled for subsequent reactions.