pH-dependent cross-coupling reactions of water-soluble organic halides with organoboron compounds catalyzed by the organometallic aqua complex [(SCS)PdII(H2O)]+ (SCS = C6H3-2,6-(CH2SBut)2)

Hidetaka Nakai, Seiji Ogo, Yoshihito Watanabe

研究成果: Contribution to journalArticle査読

45 被引用数 (Scopus)

抄録

This paper reports on the first example of pH-dependent cross-coupling reactions of water-soluble organic halides (3-X(C6H4)CC2H, where X = Cl, Br, I) with organoboron compounds (PhB(OH)2 and Ph4BNa) to form 3-Ph(C6H4)CO2H, catalyzed by the mononuclear organometallic aqua complex [(SCS)PdII(H2O)]2(SO4) ([1]2(SO4), SCS = C6H3-2,6-(CH2SBut)2) in basic media (8 < pH < 13, NaHCO3/NaOH buffers). The structure of 1(PF6) was unequivocally determined by X-ray analysis. The reactions show unique pH selectivity depending upon the organoboron compounds; i.e., the rate of the reactions with PhB(OH)2 shows a sharp maximum around pH 10, though the rate of the reactions with Ph4BNa shows a flat maximum in a pH range of about 8-11. The pH dependence is discussed on the basis of the pKa values of [1]2(SO4) and PhB(OH)2.

本文言語英語
ページ(範囲)1674-1678
ページ数5
ジャーナルOrganometallics
21
8
DOI
出版ステータス出版済み - 4 14 2002
外部発表はい

All Science Journal Classification (ASJC) codes

  • 物理化学および理論化学
  • 有機化学
  • 無機化学

フィンガープリント

「pH-dependent cross-coupling reactions of water-soluble organic halides with organoboron compounds catalyzed by the organometallic aqua complex [(SCS)Pd<sup>II</sup>(H<sub>2</sub>O)]<sup>+</sup> (SCS = C<sub>6</sub>H<sub>3</sub>-2,6-(CH<sub>2</sub>SBu<sup>t</sup>)<sub>2</sub>)」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。

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