Synthesis of bicyclo[4.1.0]heptenes via palladium-catalyzed intramolecular coupling-cyclization of 3-(cyclohexa-2,4-dienyl)pentane-2,4-dione with β-styryl bromides

Ming Chang P Yeh, Wen Cheng Tsao, Yen Jung Wang, Hui Fen Pai

研究成果: 雜誌貢獻文章

7 引文 斯高帕斯(Scopus)

摘要

Palladium-catalyzed intramolecular coupling-cyclization of 3-(cyclohexa-2,4-dienyl)pentane-2,4-dione with β-styryl bromides proceeds in regio- and stereoselective fashions to give 2-styryl-substituted bicyclo[4.1.0]hept-3-enes in good yields. The formation of the bicyclo[4.1.0]hept-3-enes was rationalized by starting with oxidative addition of Pd(PPh3)4 to the carbon-bromine bond of β-styryl bromide (RBr) to give Pd(R)BrLn. Reaction of Pd(R)BrLn with Ag 2CO3 generates a cationic RPd(II)Ln species. Chelation of the RPd(II)Ln cation to both the O-enolate of the ketone and the proximal double bond followed by attack of the enolate on the activated double bond gave a bicyclic η1-allylpalladium intermediate. The postulated bicyclic η1-allylpalladium intermediate leads to 2-styryl-substituted bicyclo[4.1.0]hept-3-enes with exclusive regio- and stereoselectivities after reductive elimination.

原文英語
頁(從 - 到)4271-4277
頁數7
期刊Organometallics
26
發行號17
DOIs
出版狀態已發佈 - 2007 八月 13

    指紋

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

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