Activation of aromatic carbon-hydrogen bonds by palladium(II) acetate-dialkyl sulfide systems. Formation and characterization of novel diphenyltripalladium(II) complexes.
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概要
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Palladium(II) acetate reacts with benzene in the presence of dialkyl sulfides at 70 °C to afford novel diphenyltripalladium(II) complexes of [(R<SUP>1</SUP>SR<SUP>2</SUP>)PhPd(μ-MeCO<SUB>2</SUB>)<SUB>2</SUB>Pd(μ-MeCO<SUB>2</SUB>)<SUB>2</SUB>PdPh(R<SUP>1</SUP>SR<SUP>2</SUP>)] (<B>1a</B>; R<SUP>1</SUP>=Bu<I><SUP>t</SUP></I>, R<SUP>2</SUP>=CH<SUB>2</SUB>Bu<I><SUP>t</SUP></I>: <B>1b</B>; R<SUP>1</SUP>=R<SUP>2</SUP>=Bu<I><SUP>i</SUP></I>: <B>1c</B>; R<SUP>1</SUP>=R<SUP>2</SUP>=Pr<I><SUP>i</SUP></I>: <B>1d</B>; R<SUP>1</SUP>=R<SUP>2</SUP>=Et). Adducts, [Pd(MeCO<SUB>2</SUB>)<SUB>2</SUB>(Bu<I><SUP>t</SUP></I>SCH<SUB>2</SUB>Bu<I><SUP>t</SUP></I>)<SUB>2</SUB>] and [Pd(MeCO<SUB>2</SUB>)<SUB>2</SUB>(SPr<I><SUP>i</SUP></I><SUB>2</SUB>)<SUB>2</SUB>], prepared by the reactions of palladium(II) acetate and the corresponding dialkyl sulfides in benzene at 5–10 °C, change to <B>1a</B> and <B>1c</B>, respectively, on heating in benzene at 70 °C. In contrast, reactions of palladium(II) acetate with toluene or thiophene in the presence of diisopropyl sulfide afford no isolable tolyl-or thienyl-palladium species, but coupling products, i.e. bitolyls or bithienyls, are detected by GLC analysis. Treatment of <B>1b</B> with styrene produces <I>trans</I>-stilbene, whereas <B>1c</B> reacts with carbon monoxide as well as carbon dioxide to yield benzoic acid. When palladium(II) acetate and <I>t</I>-butyl phenethyl sulfide are heated at 80 °C in benzene, an adduct [Pd(MeCO<SUB>2</SUB>)<SUB>2</SUB>(Bu<I><SUP>t</SUP></I>SCH<SUB>2</SUB>CH<SUB>2</SUB>Ph)<SUB>2</SUB>] is formed, in sharp contrast with the case of benzyl <I>t</I>-butyl sulfide, which gives a cyclopalladated complex under the same reaction conditions.
- 公益社団法人 日本化学会の論文
著者
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Fujiwara Yuzo
Department Of Applied Chemistry Faculty Of Engineering Hiroshima University
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Fuchita Yoshio
Department Of Chemistry Faculty Of Science Kyushu University Ropponmatsu
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Hiraki Katsuma
Department Of Applied Chemistry Faculty Of Engineering Nagasaki University
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FUJIWARA Yuzo
Department of Applied Chemistry, Faculty of Engineering, Kyushu University
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Kamogawa Yasuko
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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Suenaga Miho
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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Tohgoh Kazutaka
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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