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  • Title: Palladium-catalyzed annulation of 2,2'-diiodobiphenyls with alkynes: synthesis and applications of phenanthrenes.
    Author: Lin YD, Cho CL, Ko CW, Pulte A, Wu YT.
    Journal: J Org Chem; 2012 Nov 16; 77(22):9979-88. PubMed ID: 23078637.
    Abstract:
    A range of phenanthrene derivatives were efficiently synthesized by the palladium-catalyzed annulation of 2,2'-diiodobiphenyls with alkynes. The scope, limitations and regioselectivity of the reaction were investigated. The described method was adopted to synthesize 9,10-dialkylphenanthrenes, sterically overcrowded 4,5-disubstituted phenanthrenes and phenanthrene-based alkaloids. Reactions of highly methoxy-substituted biphenyls with 2-(2-propynyl)pyrrolidine and 2-(2-propynyl)piperidine gave 2-(9-phenanthylmethyl)pyrrolidines and 2-(9-phenanthylmethyl)piperidines, respectively. The products were transformed to phenanthroindolizidine and phenanthroquinolizidine alkaloids by the Pictet-Spengler reaction.
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