Abstract
The prospect of predictably manipulating the chemo- and stereoselectivity of metal catalysts is both aesthetically and economically attractive. The most straightforward way to affect the chemical behavior of a given metal ion is through changes in its ligands. It is well recognized that changes within the first coordination sphere of a metal ion can have a relatively dramatic impact on the properties of the entire complex. On the other hand, modifications of the ligand superstructure and substituents have subtler and somewhat more predictable effects. Such ligand modifications as applied to the coordination chemistry of tertiary phosphines have begun to receive increasing attention because of the applicability of this technology to catalysis. In this chapter, I discuss several studies which have concerned the coordination chemistry of tertiary phosphine ligands which bear chemically active substituents. This review is not comprehensive, rather the ligand systems discussed were selected because of the novel properties they impart to their complexes, the usefulness of their complexes in mechanistic or catalytic studies, or their synthetic versatility. Areas related to the theme of this review which were intentionally de-emphasized are di- and polyphosphines, chiral phosphines, and polymer-bound phosphines. These topics are covered more fully in other chapters of this book.
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References
W. S. Knowles and M. J. Sabacky, Ger. Offen. 2, 123, 063 (1971).
W. S. Knowles, M. J. Sabacky, and B. D. Vineyard, Adv. Chem. Ser. 132, 274 – 282 (1972).
B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. C. Bachman, and D. J. Weinkauff, J. Am. Chem. Soc. 99, 5946 – 5952 (1977).
E. M. Miller and B. L. Shaw, J. C. S., Dalton Trans., 480 – 485 (1974).
W. J. Louw, D. J. A. de Waal, and J. E. Chapman, J. C. S., Chem. Comm., 845 – 846 (1977).
J. C. Jeffery and T. B. Rauchfuss, Inorg. Chem. 18, 2658 – 2666 (1979).
T. B. Rauchfuss, Plat. Met. Rev. 24, 95 – 99 (1980).
N. W. Alcock, J. M. Brown, and J. C. Jeffery, J. C. S., Dalton Trans. 583 – 588 (1976).
J. Powell, A. Kuksis, C. J. May, S. C. Nyberg, and S. J. Smith, J. Am. Chem. Soc. 103, 5941 – 5943 (1981).
J. P. Collman, R. G. Finke, J. N. Cawse, and J. I. Brauman, J. Am. Chem. Soc. 100, 4766 – 4772 (1978).
For an example of true crown ether-phosphine, see E. M. Hyde, B. L. Shaw, and I. Shepherd, J. C. S., Dalton Trans., 1693 – 1705 (1978).
M. E. Wilson, R. G. Nuzzo, and G. M. Whitesides, J. Am. Chem. Soc. 100, 2269 – 2270 (1978).
M. E. Wilson and G. M. Whitesides, J. Am. Chem. Soc. 100, 306 – 307 (1978).
M. K. Cooper and J. M. Downes, Inorg. Chem. 17, 880–884 (1978); J. C. S., Chem. Comm., 381 (1981).
M. D. Fryzuk and P. A. MacNeil, J. Am. Chem. Soc. 103, 3592 – 3593 (1981).
W. Keirn, R. Appel, A. Storeck, C. Kruger, and R. Goddard, Angew. Chem. Int. Ed. Eng. 20, 116–117 (1981).
D. Houalla, J. F. Brazier, J. Sanchez, and R. Wolf, Tetrahedron Lett., 2969 – 2970 (1972).
C. Pradat, J. G. Riess, D. Bondoux, B. F. Mentzen, I. Tkatchenko, and D. Houalla, J. Am. Chem. Soc. 101, 2234–2235 (1979). D. Bondoux, B. F. Mentzen, and I. Tkatchenko, Inorg. Chem. 20, 839 – 848 (1981).
D. Bondoux, D. Houalla, C. Pradat, J. G. Riess, I. Tkatchenko, and R. Wolf, Fundarnental Research in Hornogeneous Catalysis, edited by M. Tsutsui (Pergamon Press, New York, 1979 ), Vol. 3, pp. 969 – 981.
D. M. Roundhill, R. A. Bechtold, and S. G. Roundhill, Inorg. Chem. 19, 284 – 289 (1980).
F. Jeanneaux, A. Grand, and J. G. Riess, J. Am. Chem. Soc. 103, 4272 – 4273 (1981).
P. Vierling, J. G. Riess, and A. Grand, J. Am. Chem. Soc. 103, 2466 – 2467 (1981).
W. K. Musker, Ace. Chem. Res. 13, 200 – 208 (1980).
D. St. C. Black and A. J. Hartshorn, Coord. Chem. Rev. 9, 219–274 (1972–1973).
K. Issleib and H. Zimmerman, Z. anorg. allg. Chem. 353, 197 – 206 (1967).
D. M. Singleton, P. W. Glockner, and W. Keirn, British Patent 1 364 870 (1974).
J. E. Hoots, T. B. Rauchfuss, and D. A. Wrobleski, Inorg. Syn. 21, 175 – 179 (1982).
For related patents, see also R. F. Mason, United States Patent 3 686 351 (1972) and E. F. Lutz, United States Patent 3 825615 (1974).
E. R. Freitas and C. R. Gum, Chem. Eng. Progs. 75 (1), 73 – 75 (1979).
W. Keirn, F. H. Kowaldt, R. Goddard, and C. Kruger, Angew. Chem. Int. Ed. Eng. 17, 466–467 (1978); M. Peuckert and W. Keirn, Organometal. 2, 594–597 (1983).
P. Braunstein, D. Matt, Y. Dusausoy, J. Fischer, A. Mitschler, and L. Ricard, J. Am. Chem. Soc. 103, 5115 – 5125 (1981).
T. B. Rauchfuss, Inorg. Chem. 16, 2966 – 2968 (1977).
O. Casellato, P. A. Vigato, D. E. Fenton, and M. Vidali, Chem. Soc. Rev. 8, 199 – 220 (1979).
T. B. Rauchfuss, S. R. Wilson, and D. A. Wrobleski, J. Am. Chem. Soc. 103, 6769 – 6770 (1981).
D. A. Wrobleski and T. B. Rauchfuss, J. Am. Chem. Soc. 104, 2314 – 2315 (1982).
G. P. Shiemenz and H. Kaack, Liebigs Ann. Chem., 1480 – 1495 (1973).
T. B. Rauchfuss, J. Am. Chem. Soc. 101, 1045–1047 (1979). E. F. Landvatter and T. B. Rauchfuss, Organometallics 1, 506 (1982).
T. B. Rauchfuss, Fundamental Research in Homogeneous Catalysis, edited by M. Tsutsui, (Pergamon Press, New York, 1979 ), Vol. 3, pp. 1021 – 1032.
G. D. Vaughn and J. A. Gladysz, J. Am. Chem. Soc. 103, 5608 – 5609 (1981).
T. B. Rauchfuss, J. Organometal. Chem. 162, C19 – C21 (1978).
J. E. Hoots, J. C. Jeffery, T. B. Rauchfuss, S. P. Schmidt, and P. A. Tucker, Adv. in Chem. Ser. 196, 303 – 311 (1982).
J. C. Jeffery, T. B. Rauchfuss, and P. A. Tucker, Inorg. Chem. 19, 3306 (1980).
M. A. Bennett, R. N. Johnson, G. B. Robertson, I. B. Tomkins, and P. O. Whimp, J. Am. Chem. Soc. 98, 3514–3523 (1976) and references therein.
D. Fenske and H. J. Becher, Chem. Ber. 108, 2115–2123 (1975). H. J. Becher, W. Bensmann, and D. Fenske, Chem. Ber. 110, 315 – 321 (1977).
W. Bensmann and D. Fenske, Angew. Chem. Int. Ed. Eng. 18, 677–678 (1979).
D. Fenske and A. Christidis, Angew. Chem. Int. Ed. Eng. 20, 129–131 (1981).
D. Fenske, Angew. Chem. Int. Ed. Eng. 15, 381–382 (1976).
J. P. Collman and L. S. Hegedus, Principles and Applications of Organotransition Metal Chemistry ( University Science Books, Mill Valley, CA 1980 ).
C. Charrier and F. Mathey, J. Organometal. Chem. 170, C41 – C43 (1979).
T. Hayashi, T. Mise, S. Mitachi, K. Yamamoto, and M. Kumada, Tetrahedron Lett., 1133 – 1137 (1976).
Th. Kauffmann, J. Ennen, H. Lhotak, A. Rensing, F. Steinseifer, and A. Woltermann, Angew. Chem. Int. Ed. Eng. 19, 328–329 (1980).
K. Berghus, A. Hamsen, A. Rensing, A. Woltermann, and Th. Kauffmann, Angew. Chem. Int. Ed. Eng. 20, 117–118 (1981).
N. E. Schore, J. Am. Chem. Soc. 101, 7410 – 7412 (1979).
E. P. Kyba, A. M. John, S. B. Brown, C. W. Hudson, M. J. McPhaul, A. Harding, K. Larsen, S. Niedzwiecki, and R. E. Davis, J. Am. Chem. Soc. 102, 139 – 147 (1980).
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Rauchfuss, T.B. (1983). Functionalized Tertiary Phosphines and Related Ligands in Organometallic Coordination Chemistry and Catalysis. In: Pignolet, L.H. (eds) Homogeneous Catalysis with Metal Phosphine Complexes. Modern Inorganic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3623-5_7
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