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Palladium-Catalyzed Annulation of 2,2′-Diiodobiphenyls with Alkynes: Synthesis and Applications of Phenanthrenes

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journal contribution
posted on 16.11.2012, 00:00 authored by Yu-De Lin, Chun-Lung Cho, Chih-Wei Ko, Anna Pulte, Yao-Ting Wu
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.