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Bietti M, Lanzalunga O, Lapi A, et al. Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity. J Org Chem. 2017;82(11):5761-5768doi: 10.1021/acs.joc.7b00563.
Bietti, M., Lanzalunga, O., Lapi, A., Martin, T., Mazzonna, M., Polin, M., & Salamone, M. (2017). Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity. The Journal of organic chemistry, 82(11), 5761-5768. https://doi.org/10.1021/acs.joc.7b00563
Bietti, Massimo, et al. "Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity." The Journal of organic chemistry vol. 82,11 (2017): 5761-5768. doi: https://doi.org/10.1021/acs.joc.7b00563
Bietti M, Lanzalunga O, Lapi A, Martin T, Mazzonna M, Polin M, Salamone M. Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity. J Org Chem. 2017 Jun 02;82(11):5761-5768. doi: 10.1021/acs.joc.7b00563. Epub 2017 May 17. PMID: 28481527.
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J Org Chem. 2017 Jun 02;82(11):5761-5768. doi: 10.1021/acs.joc.7b00563. Epub 2017 May 17.

Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity.

The Journal of organic chemistry

Massimo Bietti, Osvaldo Lanzalunga, Andrea Lapi, Teo Martin, Marco Mazzonna, Mariangela Polin, Michela Salamone

Affiliations

  1. Dipartimento di Scienze e Tecnologie Chimiche, Università "Tor Vergata" , Via della Ricerca Scientifica, 1, I-00133 Rome, Italy.
  2. Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, c/o Dipartimento di Chimica, Sapienza Università di Roma , P.le A. Moro, 5, I-00185 Rome, Italy.
  3. CIRCC Interuniversity Consortium of Chemical Catalysis and Reactivity , Via Celso Ulpiani 27, 70126 Bari, Italy.

PMID: 28481527 DOI: 10.1021/acs.joc.7b00563

Abstract

A change in regioselectivity has been observed in the hydrogen atom transfer (HAT) reactions from 4-alkyl-N,N-dimethylbenzylamines (alkyl = ethyl, isopropyl, and benzyl) to the phthalimide N-oxyl radical (PINO) by effect of protonation. This result can be rationalized on the basis of an acid-induced deactivation of the C-H bonds α to nitrogen toward HAT to PINO as evidenced by the 10

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