Application of the water-gas shift reaction. I. Hydrogenation and hydroformylation reactions of olefins with carbon monoxide and water catalyzed by rhodium phosphine complexes.

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概要

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• The hydrogenation of methyl crotonate with CO and H<SUB>2</SUB>O is efficiently catalyzed by RhH<SUB>2</SUB>(O<SUB>2</SUB>COH)[P(<I>i</I>-Pr)<SUB>3</SUB>]<SUB>2</SUB> or [RhCl(C<SUB>7</SUB>H<SUB>8</SUB>)]<SUB>2</SUB>/P(<I>i</I>-Pr)<SUB>3</SUB>/<I>n</I>-BuLi (C<SUB>7</SUB>H<SUB>8</SUB>=norbornadiene). Both catalyst precursors are shown to form the same active species; <I>trans</I>Rh(OH)(CO)[P(<I>i</I>-Pr)<SUB>3</SUB>]<SUB>2</SUB>. The catalytic activity of the system ([RhCl(C<SUB>7</SUB>H<SUB>8</SUB>)]<SUB>2</SUB>/phosphine/<I>n</I>-BuLi) increases with increase of the basicity of the phosphine ligands (phosphine=P(<I>i</I>-Pr)<SUB>3</SUB>>P(<I>n</I>-Bu)<SUB>3</SUB>>PPh(<I>i</I>-Pr)<SUB>2</SUB>>PPh<SUB>2</SUB>(<I>i</I>-Pr)>PPh<SUB>3</SUB>). This reaction is also applicable to the hydrogenation of the C=C bond of electronwithdrawing olefins and the C=O bond of ketones and aldehydes. Interestingly, the catalysis for the C=C bond, to which less electron-withdrawing groups are attached, gives dominantly aldehydes due to hydroformylation. The mechanism is also discussed.

• 公益社団法人 日本化学会の論文

著者

• Kobayashi Teruyuki

  Department Of Chemistry Faculty Of Science Yamagata University

• Okano Tamon

  Department Of Materials Science Faculty Of Engineering

• Kiji Jitsuo

  Department of Chemistry Faculty of Science Osaka University

• Konishi Hisatoshi

  Department of Environmental Chemistry and Technology, Faculty of Engineering, Tottori University

• Konishi Hisatoshi

  Department of Environmental Chemistry & Technology, Tottori University

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