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Copper‐Catalyzed Site‐Selective Oxidative C−C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol
Author(s) -
Vodnala Nagaraju,
Gujjarappa Raghuram,
Hazra Chinmoy K.,
Kaldhi Dhananjaya,
Kabi Arup. K.,
Beifuss Uwe,
Malakar Chandi C.
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.201801096
Subject(s) - chemistry , catalysis , bond cleavage , acylation , peptide bond , amide , cleavage (geology) , combinatorial chemistry , pyridine , copper , stereochemistry , medicinal chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering , enzyme
A copper‐catalyzed approach for the N‐acylation of anilines with acetone and acetophenones via C−C bond cleavage is described. Under the developed conditions both CHCl 3 and CH 2 Cl 2 were identified as potential C1‐source to promote the transformation. The reaction features a site selective C−C bond cleavage to install the amide moieties with high functional‐group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E‐factor (13.91 mg/1 mg) than current industrially used method (E‐factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1 H NMR as a preliminary investigation of the reaction mechanism.