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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 23
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ARTICLES

A metal-free approach to access ketones, amides, and nitriles employing TBAI/TBHP oxidative system in water

Suzane Quintana GomesDepartment of Organic Chemistry, Institute of Chemistry, University of Campinas, Campinas, São Paulo, BrazilView further author information
&
Airton G. Salles JrDepartment of Organic Chemistry, Institute of Chemistry, University of Campinas, Campinas, São Paulo, BrazilCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-9423-2552View further author information
ORCID Icon
Pages 3389-3399 | Received 13 Jul 2019, Published online: 01 Oct 2019
 
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Abstract

Hydrocarbons, benzylamines, and heteroaromatic-bearing amines have been efficiently employed as substrates in allylic and benzylic oxidations via C(sp3)–H bond activation by TBAI/TBHP in water. This operationally simple method allows access to ketones, nitriles, and amides in moderate to high yields and a regio- and chemoselective late-stage functionalization.

GRAPHICAL ABSTRACT

Additional information

Funding

We thank Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, São Paulo, Brazil) for financial support [FAPESP 2017/18400-6]. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001.

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