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

研究成果: Article

38 引文 斯高帕斯(Scopus)

摘要

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.

原文English
頁(從 - 到)9979-9988
頁數10
期刊Journal of Organic Chemistry
77
發行號22
DOIs
出版狀態Published - 2012 十一月 16

    指紋

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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