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Copper-Mediated Selective C-H Activation and Cross-Dehydrogenative C-N Coupling of 2′-Aminoacetophenones

Andivelu Ilangovan* and Gandhesiri Satish

*School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, India, Email: ilangovanbduyahoo.com

A. Ilanovan, G. Satish, Org. Lett., 2013, 15, 5726-5729.

DOI: 10.1021/ol402750r (free Supporting Information)


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Abstract

Cross-dehydrogenative C-N annulations and dealkylative C-N annulations of 2′-N-aryl/alkylaminoacetophenones and 2′-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)2ĚH2O, NaOAc and air gave isatins in good yields. However, on reaction with CuBr, 2′-N-benzylaminoacetophenones underwent selective oxidation at the benzylic position to provide the corresponding benzamides exclusively.

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Direct Amidation of 2′-Aminoacetophenones Using I2-TBHP: A Unimolecular Domino Approach toward Isatin and Iodoisatin

A. Ilangovan, G. Satish, J. Org. Chem., 2014, 79, 4984-4991.


Key Words

isatins, oxygen, copper, C-H activation, C-N coupling, benzamides


ID: J54-Y2013