Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes

Nobuhiro Kanomata, Jun Suzuki, Hironobu Kubota, Kiichiro Nishimura, Terumichi Enomoto

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

We have accomplished efficient synthesis of planar-chiral bridged 2,2′-bipyridine (S)-6, C2-symmetric bipyridinophane (S,S)-7, bridged 2,2′:6′,2″-terpyridines (S)-11, and C2-symmetric terpyridine (S,S)-12 by metal-mediated biaryl cross-coupling or homo-coupling reactions of the corresponding 6-halo[10](2,5)pyridinophanes. Stille-type and Negishi cross-coupling reactions are particularly useful for the syntheses of 6, 11, and 12. On the other hand, nickel-mediated homo-coupling reaction worked best for achieving the synthesis of structurally unique bipyridinophane 7.

Original languageEnglish
Pages (from-to)2740-2743
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number23
DOIs
Publication statusPublished - 2009 Jun 10

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes'. Together they form a unique fingerprint.

  • Cite this