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 journalArticle

36 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

Fingerprint

Phenanthrenes
Alkynes
Palladium
Alkaloids
Pyrrolidines
Piperidines
Regioselectivity
Derivatives
phenanthrene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Lin, Yu De ; Cho, Chun Lung ; Ko, Chih Wei ; Pulte, Anna ; Wu, Yao-Ting. / Palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes : Synthesis and applications of phenanthrenes. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 22. pp. 9979-9988.
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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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Palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes : Synthesis and applications of phenanthrenes. / Lin, Yu De; Cho, Chun Lung; Ko, Chih Wei; Pulte, Anna; Wu, Yao-Ting.

In: Journal of Organic Chemistry, Vol. 77, No. 22, 16.11.2012, p. 9979-9988.

Research output: Contribution to journalArticle

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