Palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes: Synthesis and applications of phenanthrenes

Yu De Lin, Chun Lung Cho, Chih Wei Ko, Anna Pulte, Yao Ting Wu

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9979-9988
Number of pages10
JournalJournal of Organic Chemistry
Volume77
Issue number22
DOIs
Publication statusPublished - 2012 Nov 16

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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