Copper-Catalyzed Site-Selective Oxidative C−C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol [11.12.18]
Original publication
Vodnala, Nagaraju; Gujjarappa, Raghuram; Hazra, Chinmoy K.; Kaldhi, Dhananjaya; Kabi, Arup. K.; Beifuss, Uwe; Malakar, Chandi C. (2018): Copper-Catalyzed Site-Selective Oxidative C−C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol. In: Adv. Synth. Catal. 116, S. 12029. DOI: 10.1002/adsc.201801096.
Author Informationen:
- Department of Chemistry, National Institute of Technology Manipur, Langol, Imphal, Manipur 795004, India
- Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon, 305-701, South Korea
- Institut für Chemie, Universität Hohenheim, Garbenstr. 30, Stuttgart, D-70599, Germany
Abstract
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 CHCl3 and CH2Cl2 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 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.). © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
