Synthesis 2017; 49(17): 3998-4006
DOI: 10.1055/s-0036-1588446
paper
© Georg Thieme Verlag Stuttgart · New York

Solvent-Free Synthesis of Salen Ligands and Pd(II)– and Cu(II)–Salen Complexes: Their Use in the Oxidation of α-Tetralones to α-Naphthols

José F. Cívicos
Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saùde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   eMail: [email protected]
,
Juliana S. M. Coimbra
Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saùde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   eMail: [email protected]
,
Paulo R. R. Costa*
Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saùde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   eMail: [email protected]om
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Publikationsverlauf

Received: 27. März 2017

Accepted after revision: 08. Mai 2017

Publikationsdatum:
27. Juni 2017 (online)


Abstract

Racemic trans-cyclohexane-1,2-diamine was allowed to react with eleven aldehydes with different patterns of substitution at the aromatic ring, in the absence of solvent, by manually milling the reagents. The corresponding imines were obtained in moderated to high chemical yields, in only 10 minutes of reaction. A one-pot, two-step preparation of stable complexes of selected imines with Pd(OAc)2 and Cu(OAc)2 and the use of these complexes as catalysts in the aromatiz­ation of methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate to the corresponding methyl 1-hydroxynaphthalene-2-carboxylates, is also reported.

Supporting Information

 
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