Original scientific paper

https://doi.org/10.5562/cca2103

Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes

Katalin Gulácsi ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
István Németh ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
Ádám Szappanos ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
Kinga Csillag ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
Tünde Zita Illyés ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
Tibor Kurtán ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20
Sándor Antus ; Department of Organic Chemistry, University of Debrecen, H-4010 Hungary, Debrecen, P.O. Box 20;Carbohydrate Research Group of Hungarian Academy Sciences, H-4010 Hungary, Debrecen, P.O. Box 20

Abstract

The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1,2-dihydronaphthalenes
(14a,b) has been studied with 2-chloromercuriphenols (5a–d) in the presence of
Li2[PdCl4] catalyst. The reactions resulted in the diastereoselective formation of racemic 6-
phenylpterocarpans of (6R, 6aR,11aR) relative configuration [(±)-8a–d] and their dibenzo[1,3]dioxocine
analogues [(±)-12a–d] as main products, respectively. The ratio of products and the lack of regioisomeric
products (13a–d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes, which has
been also supported by the transformation of 14a,b under similar conditions.(doi: 10.5562/cca2103)

Keywords

Pterocarpans; Dibenzo[d,g][1,3]dioxocines; Palladium(0); Oxidative coupling; Reaction mechanism; Catalysis

Hrčak ID:

105381

URI

https://hrcak.srce.hr/105381

Publication date:

1.7.2013.

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