CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0091-0096
DOI: 10.1055/s-0036-1588550
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Palladium-Catalyzed α-Arylation of Dimethyl Malonate and Ethyl Cyanoacetate with o-Alkoxybromobenzenes for the Synthesis of Phenylacetic Acid, Esters and Phenylacetonitriles

José F. Cívicosa, Paulo R. R. Costa*a, Jorge L. O. Domingos*b
  • aInstituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
  • bDep. Química Orgânica, Instituto de Química, Centro de Tecnologia e Ciências, Universidade do Estado do Rio de Janeiro, 20550-900, Rio de Janeiro, RJ, Brazil
We thank the Brazilian agencies Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES; BJT-2014), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), and Fundação Carlos­ Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ).
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Publication History

Received: 28 July 2017

Accepted after revision: 01 August 2017

Publication Date:
22 August 2017 (online)

Abstract

α-Aryl malonate and α-aryl cyano acetate moieties are found in the structures of many bioactive compounds. They are also key intermediates for the synthesis of many compounds such as isoflavonoids. In this work, we synthesized these compounds, with different patterns of substitution, starting with the palladium-catalyzed reaction of o-alkoxy-bromoarenes with dimethyl malonate or ethyl cyanoacetate. Under the conditions applied, moderate to good yields of arylmalonate mono­esters, phenylacetic esters or acids, and benzylnitrile derivatives were obtained.

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