Reaction of coordinated phosphines. III. Reaction of phenyl compounds of typical groups V and VI elements with palladium(II) salts in the presence of olefinic compounds.
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概要
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The reaction of phenyl compounds of typical groups V and VI elements, Ph<I><SUB>n</SUB></I>A and Ph<I><SUB>n</SUB></I>AX<SUB>2</SUB> (<I>n</I>=2, 3; A=P, As, Sb, Bi, S, Se, Te; X=Cl or X<SUB>2</SUB>=O), with Pd(II) salts was studied in the presence of olefinic compounds (1-octene and ethyl acrylate) in acetonitrile. The phenyl migration from A to Pd to produce phenylpalladium species, which lead to the phenylation of olefin, was observed for all Ph<I><SUB>n</SUB></I>A and Ph<I><SUB>n</SUB></I>AX<SUB>2</SUB> (except for A=S and Ph<SUB>3</SUB>PX<SUB>2</SUB>) when Pd(OAc)<SUB>2</SUB> was utilized. The reaction, however, was inhibited or greatly suppressed for the compounds of P and As when PdCl<SUB>2</SUB> was used in place of Pd(OAc)<SUB>2</SUB>. The compounds of Sb and Bi readily react with PdCl<SUB>2</SUB>. Mechanistic discussion was given in terms of the extent of nucleophilic assistance by acetate ion when Pd(II) attacks the aromatic nucleus electrophilically at the carbon atom bonded to A.
- 公益社団法人 日本化学会の論文
著者
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MATSUDA Tsutomu
Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa University
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Kikukawa Kiyoshi
Department Of Biological And Environmental Chemistry Kinki University
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Takagi Makoto
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Kawamura Teruo
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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