Synthesis 2015; 47(22): 3505-3512
DOI: 10.1055/s-0034-1378745
paper
© Georg Thieme Verlag Stuttgart · New York

Ligand-Free Palladium-Catalyzed Oxyarylation of Dihydronaphthal­enes and Chromenequinone with o-Iodophenols and 3-Iodolawsone in PEG-400: An Efficient Synthesis of 5-Carbapterocarpans and Pterocarpanquinones

Paula de Freitas de Moraes
a  Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
,
Francisco V. Gaspar
a  Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
,
Rackel H. F. Borges
a  Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
,
Chaquip D. Netto
b  Laboratório de Química, �Universidade Federal do Rio de Janeiro, campus Macaé, RJ, Brazil
,
Raquel A. C. Leão
a  Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
,
Carmen Nájera
c  Departamento de Química Orgánica, Facultad de Ciencias and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, apdo. 99, 03080-Alicante, Spain
,
Paulo R. R. Costa*
a  Laboratório de Química Bioorgânica, Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco H, Ilha da Cidade Universitária, 21941-590, Rio de Janeiro, RJ, Brazil   Email: prrcosta2011@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 01 April 2015

Accepted after revision: 23 June 2015

Publication Date:
11 September 2015 (online)


Abstract

Dihydronaphthalenes were oxyarylated with o-iodophenols, in PEG-400 at 140 or 170 °C, leading regio- and stereoselectively to 5-carbapterocarpans. By using Pd(OAc)2 (5–10 mol%) as precatalyst and Ag2CO3 (1.1 equiv) as base (conditions A), products were obtained in good to excellent chemical yields, in 5–30 minutes, irrespective of the pattern of substitution the starting materials. Alternatively, when p-hydroxyacetophenone oxime derived palladacycle (1 mol%) was used as precatalyst, and dicyclohexylamine (2 equiv) was used as base (silver-free, conditions B), the corresponding adducts were obtained in moderate to good yields, in 0.5 to 4 hours. Finally, the oxyarylation of dihydronaphthalenes­ and chromenquinone with o-iodophenols and 3-iodolawsone in PEG-400 under conditions A led regio- and stereoselectively to the formation of carbapterocarpanquinones and pterocarpanquinones in moderate yield.

Supporting Information

 
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