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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 6phenylpterocarpans 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)

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