Metal-catalyzed cascade reactions: Useful synthetic tools for the preparation of polycyclic arenes

Chieh Ning Feng, Ya Chu Hsieh, Yao Ting Wu

研究成果: Article

13 引文 斯高帕斯(Scopus)

摘要

This account summarizes our recent efforts to synthesize numerous important and interesting polycyclic arenes under mild conditions using metal-catalyzed protocols. The palladium-catalyzed annulations of 2-iodobiphenyls or 2,2-diiodobiphenyls with alkynes efficiently generated phenanthrene derivatives. This synthetic method was utilized as the key step when preparing phenanthrene-based alkaloids, tetrabenzopyracylenes and persubstituted [8]circulenes. Depending on whether a palladium or nickel catalytic system was used, 1-ethynyl-8-iodonaphthalenes underwent either a cyclodimerization or a nitrile-incorporated cascade reaction to produce zethrenes or pyrroloarenes, respectively. Methylene-bridged polyarenes are generated easily from 2-halo-2-methylbiaryls through benzylic C-H bond activation and subsequent carbon-carbon bond formation, and palladium complexes promote the arylation of methylene carbons. The palladium-catalyzed annulations of 1,8-bis(arylethynyl)naphthalene derivatives with o-diiodoarenes yielded benzo[κ]fluoranthene-based linear acenes, which can be applied to synthesize highly curved fragments of fullerenes. The self-reactions of diarylethynes formed either dihydrocyclopenta[a]indenes or octaaryl-1,3,5,7-octatetraenes through palladium-catalyzed cycloisomerization or nickel-catalyzed tetramerization, respectively. In the presence of palladium catalysts, the hydroalkynylation of terminal arylalkynes directly generated angular trimerization adduct dienynes.

原文English
頁(從 - 到)266-279
頁數14
期刊Chemical Record
15
發行號1
DOIs
出版狀態Published - 2015 二月

    指紋

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biochemistry
  • Chemical Engineering(all)
  • Materials Chemistry

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