Syntheses of aryl- and arylethynyl-substituted N-confused porphyrins

Tomoya Ishizuka, Hiroki Yamasaki, Atsuhiro Osuka, Hiroyuki Furuta

    研究成果: Contribution to journalArticle査読

    34 被引用数 (Scopus)

    抄録

    Palladium-catalyzed cross-coupling reactions under Suzuki, Sonogashira, and Stille conditions afford 3-aryl (9-12) and 3-arylethynyl N-confused porphyrin (NCP) silver(III) complexes (13-15) from the 3-bromo NCP complex (4) in ca. 70% yields along with the transmetalated products, 3-substituted NCP palladium(II) complexes (11-Pd to 15-Pd), in 10-30% yields. Substitution at 3-position was confirmed by the single crystal X-ray structures of 9, 13-Ag, and 13-Pd. The arylethynyl groups or five-membered heterocyclic aromatic rings at 3-position largely affected the optical properties of N-confused porphyrin, in which the longest absorption maxima of the Q-bands are shifted bathochromically by 30-120 nm. The electronic effect of substituent differs largely between palladium and silver complexes reflecting the different π-electron delocalization pathway of NCP cores. 3-Aryl- and 3-arylethynyl NCP silver(III) complexes were easily demetalated to afford the corresponding free base porphyrins by the treatment of sodium borohydride.

    本文言語英語
    ページ(範囲)5137-5147
    ページ数11
    ジャーナルTetrahedron
    63
    24
    DOI
    出版ステータス出版済み - 6 11 2007

    All Science Journal Classification (ASJC) codes

    • 生化学
    • 創薬
    • 有機化学

    フィンガープリント

    「Syntheses of aryl- and arylethynyl-substituted N-confused porphyrins」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

    引用スタイル