Nickel-catalyzed, cascade cycloadditions of 1-ethynyl-8-halonaphthalenes with nitriles: Synthesis, structure, and physical properties of new pyrroloarenes

Tsun Cheng Wu, Chia Cheng Tai, Hsin Chieh Tiao, Ming Yu Kuo, Yao Ting Wu

研究成果: Article

8 引文 斯高帕斯(Scopus)

摘要

The reaction of 1-ethynyl-8-halonaphthalenes 1 with nitriles in the presence of the catalytic system [NiBr2(dppe)]/Zn (dppe=1,2-bis(diphenylphosphino)ethane) is found to produce unusual pyrroloarenes 2. The carbon-nitrogen triple bond in nitrile is activated twice, and five new bonds are formed in a one-pot transformation, which causes a pyrrole and two six-membered rings to be generated simultaneously. The scope and limitations of this reaction are examined. Similarly, alkyl-bridged diynes also furnish the corresponding polycycles. Diaryl-substituted cycloadducts 2 (R 1=Ar) are fluxional, because of the restriction in rotation of the aryl groups. The rotational barrier is studied by performing 1Ha NMR experiments at various temperatures. The structures of several compounds are determined by X-ray crystallographic analysis. The photophysical and electrochemical properties of the pyrroloarenes are also investigated. (Ni)triles and tribulations: The reaction of 1-ethynyl-8-halonaphthalenes 1 with nitriles in the presence of the catalytic system [NiBr2(dppe)]/Zn (dppe=1,2-bis(diphenylphosphino)ethane) produces unusual pyrroloarenes 2, which have unusual structures (see scheme) and exhibit interesting physical properties. The diluted solutions of these pyrroloarenes are strongly fluorescent, even under ambient light.

原文English
頁(從 - 到)1930-1935
頁數6
期刊Chemistry - A European Journal
17
發行號6
DOIs
出版狀態Published - 2011 十二月 7

    指紋

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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