Palladium-catalyzed arylation of methylene-bridged polyarenes

Synthesis and structures of 9-arylfluorene derivatives

Jheng Jhih Chen, Satoru Onogi, Ya Chu Hsieh, Chien Chi Hsiao, Shuhei Higashibayashi, Hidehiro Sakurai, Yao Ting Wu

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

In the presence of a catalytic system comprised of palladium(II) acetate and tricyclohexylphosphine, the reaction of fluorene with haloarenes generated 9-arylfluorenes in good to excellent yields. The scope and limitations of the coupling reaction were investigated. This synthetic protocol is more efficient than conventional methods. A wide range of functional groups, including alkyl, alkoxy, ester, and nitrile, can tolerate the reaction conditions herein. Sterically congested haloarenes also gave satisfactory results. Furthermore, this synthetic method is utilized to prepare 9,9-diarylfluorenes and tetraarylindenofluorene. Depending on the reaction conditions, the arylation of bowl-shaped sumanene gave monoarylated sumanene either as the sole product or with another diaryl-substituted product.

Original languageEnglish
Pages (from-to)1551-1558
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number8
DOIs
Publication statusPublished - 2012 May 21
Externally publishedYes

Fingerprint

Palladium
Functional groups
Esters
Derivatives
Nitriles
sumanene
fluorene
palladium(II) acetate
alkoxyl radical

Keywords

  • arylation
  • fluorenes
  • indenofluorenes
  • palladium
  • polyarenes
  • sumanene

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Palladium-catalyzed arylation of methylene-bridged polyarenes : Synthesis and structures of 9-arylfluorene derivatives. / Chen, Jheng Jhih; Onogi, Satoru; Hsieh, Ya Chu; Hsiao, Chien Chi; Higashibayashi, Shuhei; Sakurai, Hidehiro; Wu, Yao Ting.

In: Advanced Synthesis and Catalysis, Vol. 354, No. 8, 21.05.2012, p. 1551-1558.

Research output: Contribution to journalArticle

Chen, Jheng Jhih ; Onogi, Satoru ; Hsieh, Ya Chu ; Hsiao, Chien Chi ; Higashibayashi, Shuhei ; Sakurai, Hidehiro ; Wu, Yao Ting. / Palladium-catalyzed arylation of methylene-bridged polyarenes : Synthesis and structures of 9-arylfluorene derivatives. In: Advanced Synthesis and Catalysis. 2012 ; Vol. 354, No. 8. pp. 1551-1558.
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