TY - JOUR
T1 - Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes
AU - Kanomata, Nobuhiro
AU - Suzuki, Jun
AU - Kubota, Hironobu
AU - Nishimura, Kiichiro
AU - Enomoto, Terumichi
N1 - Funding Information:
The authors greatly acknowledge financial support by JSPS Grant-in-Aid for Scientific Research (C) (19550112).
PY - 2009/6/10
Y1 - 2009/6/10
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2009.03.095
DO - 10.1016/j.tetlet.2009.03.095
M3 - Article
AN - SCOPUS:64549111258
SN - 0040-4039
VL - 50
SP - 2740
EP - 2743
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 23
ER -