pH-dependent transfer hydrogenation of water-soluble carbonyl compounds with [Cp*IrIII(H2O)3]2+ (Cp* = η5C5Me5) as a catalyst precursor and HCOONa as a hydrogen donor in water

Organometallics

Volumn 18, Issue 26, 1999, Pages 5470-5474

  Ogo, Seiji ^a   Makihara, Nobuyuki ^a   Watanabe, Yoshihito ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000011348     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9903689     Document Type: Article

References (53)

1. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
2. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
3. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
4. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
5. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
6. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
7. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
8. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
9. Reviews: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994, p 287, and references therein. (b) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic Publishers: Dordrecht, 1995; p 317, and references therein. (c) Roundhill D. M. Adv. Organomet. Chem. 1995, 38, 155-188, and references therein. (d) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26, and references therein. (e) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH, Weinheim, 1998; p 615, and references therein. (f) Herrmann, W. A.; Kulpe, J. A.; Kellner, J.; Riepl, H.; Bahrmann, H.; Konkol, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 391-393, and references therein. (g) Hermann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544, and references therein. (h) Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein. (i) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310, and references therein. (j) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45, and references therein.
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32. + (M = Rh, Ir) in aqueous media has been reported. (a) Cook, J.; Hamlin, J. E.; Mutton, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1981, 2342-2352. (b) Cook, J.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1981, 924-925. (c) Cook, J.; Hamlin, J. E.; Nutton, A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1980, 144-145.
33. + (M = Rh, Ir) in aqueous media has been reported. (a) Cook, J.; Hamlin, J. E.; Mutton, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1981, 2342-2352. (b) Cook, J.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1981, 924-925. (c) Cook, J.; Hamlin, J. E.; Nutton, A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1980, 144-145.
34. + (M = Rh, Ir) in aqueous media has been reported. (a) Cook, J.; Hamlin, J. E.; Mutton, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1981, 2342-2352. (b) Cook, J.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1981, 924-925. (c) Cook, J.; Hamlin, J. E.; Nutton, A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1980, 144-145.
35. White, C.; Yates, A.; Maitlis, P. M. Inorg. Synth. 1992, 29, 228-234.
36. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-116597. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax (+44)1223-336-033; e-mail deposit@ ccdc.cam.ac.uk).
37. (a) Armstrong, R. S.; Beattie, J. K.; Best, S. P.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1983, 1973-1975.
38. (b) Flenburg, C.; Simonsen, K.; Skov, L. K. Acta Chem. Scand. 1993, 47, 862-866.
39. 2O = 15H/6H.
40. (a) DSS = sodium 2,2-dimethyl-2-silapentane-5-suifonate.
41. 2O in the range of pH 1.0-12.0.
42. 2O in the range of pH 1.0-12.0.
43. Nutton, A.; Bailey, P. M.; Maitlis, P. M. J. Chetn. Soc., Dalton Trans. 1981, 1997-2002.
44. 2O in the range of pH 1.0-12.0.
45. For example: (a) S-Penne, J. In Reductions by the Alumino-and Borohydrides in Organic Synthesis; Wiley-VCH: 1997; p 224, and references therein. (b) Lane, C. F. In Selections from the Aldrichimica Acta; Aldrich Chemical Co., Inc, 1984; pp 67-74, and references therein.
46. For example: (a) S-Penne, J. In Reductions by the Alumino-and Borohydrides in Organic Synthesis; Wiley-VCH: 1997; p 224, and references therein. (b) Lane, C. F. In Selections from the Aldrichimica Acta; Aldrich Chemical Co., Inc, 1984; pp 67-74, and references therein.
47. 4: White, C.; Oliver, A. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1973, 1901-1907.
48. 4: White, C.; Oliver, A. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1973, 1901-1907.
49. 4: White, C.; Oliver, A. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1973, 1901-1907.
50. Shimadzu gas chromatograph, GC-8A with porapac-T column.
51. 1H NMR spectra.
52. Concentration ratios to maximize the rate of the formation of the products: [HCOONa]/[1] = 50 or [substrate]/[1] = 100.
53. Parkin, S.; Moezzi, B.; Hope, H. J. Appl. Crystallogr. 1995, 28, 53-56.