β-Cyclodextrin-Modified Diphosphanes as Ligands for Supramolecular Rhodium Catalysts

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 8, 1997, Pages 865-867

  Reetz, Manfred T ^a   Waldvogel, Siegfried R ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Cyclodextrins; Hydroformylations; Hydrogenations; Phase transfer catalysis; Rhodium

Indexed keywords

EID: 0030911171     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708651     Document Type: Article

References (47)

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21. Transition metals such as copper and zinc have often been coupled with receptors such as β-cyclodextrins [11] or bound in the form of metallomicelles, mainly with the goal, however, of catalyzing the hydrolysis of carboxylates or phosphate esters [4]: a) F. M. Menger, L. H. Gan, E. Johnson, D. H. Durst, J. Am. Chem. Soc. 1987, 109, 2800; b) P. Scrimin, P. Tecilla, U. Tonellato, ibid. 1992, 114, 5086; c) M. C. Cleij; P. Scrimin, P. Tecilla, U. Tonellato, Langmuir 1996, 12, 2956; d) J. G. J. Weijnen, A. Koudijs, P. G. J. A. Tap, J. F. J. Engbersen, Recl. Trav. Chim. Pays-Bas 1993, 112, 525.
22. Transition metals such as copper and zinc have often been coupled with receptors such as β-cyclodextrins [11] or bound in the form of metallomicelles, mainly with the goal, however, of catalyzing the hydrolysis of carboxylates or phosphate esters [4]: a) F. M. Menger, L. H. Gan, E. Johnson, D. H. Durst, J. Am. Chem. Soc. 1987, 109, 2800; b) P. Scrimin, P. Tecilla, U. Tonellato, ibid. 1992, 114, 5086; c) M. C. Cleij; P. Scrimin, P. Tecilla, U. Tonellato, Langmuir 1996, 12, 2956; d) J. G. J. Weijnen, A. Koudijs, P. G. J. A. Tap, J. F. J. Engbersen, Recl. Trav. Chim. Pays-Bas 1993, 112, 525.
23. Transition metals such as copper and zinc have often been coupled with receptors such as β-cyclodextrins [11] or bound in the form of metallomicelles, mainly with the goal, however, of catalyzing the hydrolysis of carboxylates or phosphate esters [4]: a) F. M. Menger, L. H. Gan, E. Johnson, D. H. Durst, J. Am. Chem. Soc. 1987, 109, 2800; b) P. Scrimin, P. Tecilla, U. Tonellato, ibid. 1992, 114, 5086; c) M. C. Cleij; P. Scrimin, P. Tecilla, U. Tonellato, Langmuir 1996, 12, 2956; d) J. G. J. Weijnen, A. Koudijs, P. G. J. A. Tap, J. F. J. Engbersen, Recl. Trav. Chim. Pays-Bas 1993, 112, 525.
24. For a Rh-containing receptor that selectively binds and hydrogenates substrates such as allyl catechol by hydrogen bonding, see: a) H. K. A. C. Coolen, P. W. N. M. van Leeuwen, R. J. M. Nolte, Angew. Chem. 1992, 104, 906; Angew. Chem. Int. Ed. Engl. 1992, 31, 905; b) H. K. A. C. Coolen, J. A. M. Meeuwis, P. W. N. M. van Leeuwen, R. J. M. Nolte, J. Am. Chem. Soc. 1995, 117, 11 906.
25. For a Rh-containing receptor that selectively binds and hydrogenates substrates such as allyl catechol by hydrogen bonding, see: a) H. K. A. C. Coolen, P. W. N. M. van Leeuwen, R. J. M. Nolte, Angew. Chem. 1992, 104, 906; Angew. Chem. Int. Ed. Engl. 1992, 31, 905; b) H. K. A. C. Coolen, J. A. M. Meeuwis, P. W. N. M. van Leeuwen, R. J. M. Nolte, J. Am. Chem. Soc. 1995, 117, 11 906.
26. For a Rh-containing receptor that selectively binds and hydrogenates substrates such as allyl catechol by hydrogen bonding, see: a) H. K. A. C. Coolen, P. W. N. M. van Leeuwen, R. J. M. Nolte, Angew. Chem. 1992, 104, 906; Angew. Chem. Int. Ed. Engl. 1992, 31, 905; b) H. K. A. C. Coolen, J. A. M. Meeuwis, P. W. N. M. van Leeuwen, R. J. M. Nolte, J. Am. Chem. Soc. 1995, 117, 11 906.
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35. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
36. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
37. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
38. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
39. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
40. Reviews on cyclodextrins: a) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; b) M. L. Bender, M. Komiyama, Cyclodexirin Chemistry, Springer, Berlin, 1978; c) I. Tabuschi, Pure Appl. Chem. 1986, 58, 1529; d) R. Breslow, Science 1982, 218, 532; e) C. J. Easton, S. F. Lincoln, Chem. Soc. Rev. 1996, 25, 163.
41. 3 as rhodium ligands (Ruhrchemie AG) cannot be easily extended to homologous olefins such as 1-octene, [13] since these show low solubilities in water: a) B. Cornils, E. G. Kuntz,. J. Organomet. Chem. 1995, 502, 177; b) G. Papadogianakis, R. A. Sheldon, New J. Chem. 1996, 20, 175.
42. 3 as rhodium ligands (Ruhrchemie AG) cannot be easily extended to homologous olefins such as 1-octene, [13] since these show low solubilities in water: a) B. Cornils, E. G. Kuntz,. J. Organomet. Chem. 1995, 502, 177; b) G. Papadogianakis, R. A. Sheldon, New J. Chem. 1996, 20, 175.
43. Monflier et al. recently modified the Ruhrchemie AG [12] procedure by using O-alkylated β-CD additives (10-14 fold excess) to enhance the solubility; thus, substrates such as 1-octene or 1-decene can be converted, but not nonreactive internal olefins such as 3-hexene: a) E. Monflier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269; b) E. Monflier, S. Tilloy, G. Fremy, Y. Castanet, A. Mortreux, Tetrahedron Lett. 1995, 36, 9481; c) J. R. Anderson, E. M. Campi, W. R. Jackson, Catal. Lett. 1991, 9, 55.
44. Monflier et al. recently modified the Ruhrchemie AG [12] procedure by using O-alkylated β-CD additives (10-14 fold excess) to enhance the solubility; thus, substrates such as 1-octene or 1-decene can be converted, but not nonreactive internal olefins such as 3-hexene: a) E. Monflier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269; b) E. Monflier, S. Tilloy, G. Fremy, Y. Castanet, A. Mortreux, Tetrahedron Lett. 1995, 36, 9481; c) J. R. Anderson, E. M. Campi, W. R. Jackson, Catal. Lett. 1991, 9, 55.
45. Monflier et al. recently modified the Ruhrchemie AG [12] procedure by using O-alkylated β-CD additives (10-14 fold excess) to enhance the solubility; thus, substrates such as 1-octene or 1-decene can be converted, but not nonreactive internal olefins such as 3-hexene: a) E. Monflier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269; b) E. Monflier, S. Tilloy, G. Fremy, Y. Castanet, A. Mortreux, Tetrahedron Lett. 1995, 36, 9481; c) J. R. Anderson, E. M. Campi, W. R. Jackson, Catal. Lett. 1991, 9, 55.
46. Monflier et al. recently modified the Ruhrchemie AG [12] procedure by using O-alkylated β-CD additives (10-14 fold excess) to enhance the solubility; thus, substrates such as 1-octene or 1-decene can be converted, but not nonreactive internal olefins such as 3-hexene: a) E. Monflier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269; b) E. Monflier, S. Tilloy, G. Fremy, Y. Castanet, A. Mortreux, Tetrahedron Lett. 1995, 36, 9481; c) J. R. Anderson, E. M. Campi, W. R. Jackson, Catal. Lett. 1991, 9, 55.
47. 4 and filtered.