Synthesis and coordination chemistry of macrocyclic phosphine ligands

Coordination Chemistry Reviews

Volumn 255, Issue 23-24, 2011, Pages 2860-2881

  Swor, Charles D ^a   Tyler, David R ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Ligand synthesis; Macrocyclic ligands; Phosphines; Reactions of coordinated ligands; Template synthesis

Indexed keywords

EID: 80055051891     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2011.06.002     Document Type: Review

References (112)

1. Spessard G.O., Miessler G.L. Organometallic Chemistry 1997, Prentice-Hall, Upper Saddle River, NJ.
2. Crabtree R.H. The Organometallic Chemistry of the Transition Metals 2009, John Wiley and Sons. 5th ed.
3. Fey N., Orpen A.G., Harvey J.N. Coord. Chem. Rev. 2009, 253:704.
4. van Leeuwen P.W. Homogeneous Catalysis: Understanding the Art 2004, Kluwer Academic Publishers, Dordrecht.
5. Pignolet L. Homogeneous Catalysis with Metal Phosphine Complexes 1983, Plenum Press, New York.
6. Tolman W. Activation of Small Molecules: Organometallic and Bioinorganic Perspectives 2006, Wiley-VCH, Weinheim.
7. Cabbiness D.K., Margerum D.W. J. Am. Chem. Soc. 1969, 91:6540.
8. Izatt R.M., Bradshaw J.S., Nielsen S.A., Lamb J.D., Christensen J.J., Sen D. Chem. Rev. 1985, 85:271.
9. Izatt R.M., Pawlak K., Bradshaw J.S., Bruening R.L. Chem. Rev. 1991, 91:1721.
10. Busch D.H., Farmery K., Goedken V.L., Katovic V., Melnyk A.C., Sperati C.R., Tokel N. Bioinorganic Chemistry 1971, 44. American Chemical Society.
11. Clay R.M., Corr S., Micheloni M., Paoletti P. Inorg. Chem. 1985, 24:3330.
12. Frensdorff H.K. J. Am. Chem. Soc. 1971, 93:600.
13. Haymore B.L., Lamb J.D., Izatt R.M., Christensen J.J. Inorg. Chem. 1982, 21:1598.
14. Sokol L.S.W.L., Ochrymowycz L.A., Rorabacher D.B. Inorg. Chem. 1981, 20:3189.
15. Desper J.M., Gellman S.H., Wolf R.E., Cooper S.R. J. Am. Chem. Soc. 1991, 113:8663.
16. Toulhoat C., Vidal M., Vincens M. Phosphorus Sulfur Silicon Relat. Elem. 1992, 71:127.
17. Lambert B., Desreux J.F. Synthesis 2000, 1668.
18. Simulescu V., Ilia G. J. Inclus. Phenom. Macrocycl. Chem. 2010, 66:3.
19. Caminade A., Majoral J.P. Chem. Rev. 1994, 94:1183.
20. Markovskii L.N., Kal'chenko V.I. Zh. Vses. Khim. O.-Va. Im. D I Mendeleeva 1985, 30:528.
21. Tsvetkov E.N., Bovin A.N., Syundyukova V.K. Russ. Chem. Rev. 1988, 57:776.
22. Horner L., Kunz H., Walach P. Phosphorus 1975, 6:63.
23. Horner L., Walach P., Kunz H. Phosphorus Sulfur Silicon Relat. Elem. 1978, 5:171.
24. Kyba E.P., Hudson C.W., McPhaul M.J., John A.M. J. Am. Chem. Soc. 1977, 99:8053.
25. Vögtle F. Chem. Ind. (Lond.) 1972, 346.
26. Vögtle F., Wittig G. J. Chem. Ed. 1973, 50:650.
27. Davis R.E., Hudson C.W., Kyba E.P. J. Am. Chem. Soc. 1978, 100:3642.
28. Kyba E.P., John A.M., Brown S.B., Hudson C.W., McPhaul M.J., Harding A., Larsen K., Niedzwiecki S., Davis R.E. J. Am. Chem. Soc. 1980, 102:139.
29. Kyba E.P., Davis R.E., Hudson C.W., John A.M., Brown S.B., McPhaul M.J., Liu L., Glover A.C. J. Am. Chem. Soc. 1981, 103:3868.
30. Kyba E.P., Clubb C.N., Larson S.B., Schueler V.J., Davis R.E. J. Am. Chem. Soc. 1985, 107:2141.
31. Kyba E.P., Davis R.E., Fox M.A., Clubb C.N., Liu S.T., Reitz G.A., Scheuler V.J., Kashyap R.P. Inorg. Chem. 1987, 26:1647.
32. Kyba E.P., Liu S.T. Inorg. Chem. 1985, 24:1613.
33. Ciampolini M., Dapporto P., Nardi N., Zanobini F. J. Chem. Soc., Chem. Commun. 1980, 177.
34. Ciampolini M., Dapporto P., Dei A., Nardi N., Zanobini F. Inorg. Chem. 1982, 21:489.
35. Ciampolini M., Dapporto P., Nardi N., Zanobini F. Inorg. Chim. Acta 1980, 45:L239.
36. Ciampolini M., Nardi N., Zanobini F., Cini R., Orioli P.L. Inorg. Chim. Acta 1983, 76:L17.
37. Laurent B.A., Grayson S.M. Chem. Soc. Rev. 2009, 38:2202.
38. Vincens M., Grimaldo-Moron J.T., Vidal M. Tetrahedron 1991, 47:403.
39. Venkataramu S.D., El-Deek M., Berlin K.D. Tetrahedron Lett. 1976, 17:3365.
40. Vincens M., Grimaldo Moron J.T., Pasqualini R., Vidal M. Tetrahedron Lett. 1987, 28:1259.
41. Toulhoat C., Vincens M., Vidal M. Bull. Soc. Chim. Fr. 1993, 130:647.
42. Vincens M., Gong-Cheng F., Toulhoat C., Grimaldo-Moron J.T., Vidal M. Tetrahedron Lett. 1988, 29:6247.
43. Li G.Q., Govind R. Inorg. Chim. Acta 1995, 231:225.
44. Toulhoat C., Vidal M., Vincens M. Phosphorus Sulfur Silicon Relat. Elem. 1993, 78:119.
45. Baechler R.D., Mislow K. J. Am. Chem. Soc. 1970, 92:3090.
46. Laporte F., Mercier F., Ricard L., Mathey F. J. Am. Chem. Soc. 1994, 116:3306.
47. Egan W., Tang R., Zon G., Mislow K. J. Am. Chem. Soc. 1971, 93:6205.
48. Avarvari N., Mézailles N., Ricard L., Floch P.L., Mathey F. Science 1998, 280:1587.
49. Avarvari N., Maigrot N., Ricard L., Mathey F., Le Floch P. Chem. Eur. J. 1999, 5:2109.
50. Mézailles N., Maigrot N., Hamon S., Ricard L., Mathey F., Le Floch P. J. Org. Chem. 2001, 66:1054.
51. Morisaki Y., Ouchi Y., Fukui T., Naka K., Chujo Y. Tetrahedron Lett. 2005, 46:7011.
52. Collman J.P., Schneider P.W. Inorg. Chem. 1966, 5:1380.
53. Kalligeros G.A., Blinn E.L. Inorg. Chem. 1972, 11:1145.
54. Busch D.H. Acc. Chem. Res. 1978, 11:392.
55. Rosen W., Busch D.H. Inorg. Chem. 1970, 9:262.
56. Lowry D.J., Helm M.L. Inorg. Chem. 2010, 49:4732.
57. Mason L.J., Moore A.J., Carr A., Helm M.L. Heteroatom Chim. 2007, 18:675.
58. Mizuta T., Onishi M., Miyoshi K. Organometallics 2000, 19:5005.
59. Mizuta T., Aotani T., Imamura Y., Kubo K., Miyoshi K. Organometallics 2008, 27:2457.
60. Balueva A.S., Kuznetsov R.M., Litvinov I.A., Gubaidullin A.T., Nikonov G.N. Mendeleev Commun. 2000, 10:120.
61. Balueva A.S., Kuznetsov R.M., Ignatéva S.N., Karasik A.A., Gubaidullin A.T., Litvinov I.A., Sinyashin O.G., Loennecke P., Hey-Hawkins E. Dalton Trans. 2004, 442.
62. Naumov R.N., Karasik A.A., Kanunnikov F.B., Kozlov A.V., Latypov S.K., Domasevitch K.V., Hey-Hawkins E., Sinyashin O.G. Mendeleev Commun. 2008, 18:80.
63. Karasik A.A., Kulikov D.V., Balueva A.S., Ignatéva S.N., Kataeva O.N., Lönnecke P., Kozlov A.V., Latypov S.K., Hey-Hawkins E., Sinyashin O.G. Dalton Trans. 2009, 490.
64. Latypov S.K., Kozlov A.V., Hey-Hawkins E., Balueva A.S., Karasik A.A., Sinyashin O.G. J. Phys. Chem. A 2010, 114:2588.
65. Naumov R.N., Karasik A.A., Sinyashin O.G., Loennecke P., Hey-Hawkins E. Dalton Trans. 2004, 357.
66. Naumov R.N., Karasik A.A., Kanunnikov K.B., Kozlov A.V., Latypov S.K., Domasevitch K.V., Hey-Hawkins E., Sinyashin O.G. Mendeleev Commun. 2008, 18:80.
67. Naumov R.N., Kozlov A.V., Kanunnikov K.B., Gomez-Ruiz S., Hey-Hawkins E., Latypov S.K., Karasik A.A., Sinyashin O.G. Tetrahedron Lett. 2010, 51:1034.
68. Naumov R.N., Karasik A.A., Kozlovi A.V., Latypov S.K., Krivolapov D.B., Dobrynin A.B., Litvinov I.A., Kataeva O.N., Sinyashin O.G., Loennecke P., Hey-Hawkins E. Phosphorus Sulfur Silicon Relat. Elem. 2008, 183:456.
69. Karasik A.A., Naumov R.N., Spiridonova Y.S., Sinyashin O.G., Lönnecke P., Hey-Hawkins E. Z. Anorg. Allg. Chem. 2007, 633:205.
70. Laughrey Z.R., Gibb B.C. Top. Curr. Chem. 2005, 249:67.
71. Glueck D.S. Dalton Trans. 2008, 5276.
72. Diel B.N., Haltiwanger R.C., Norman A.D. J. Am. Chem. Soc. 1982, 104:4700.
73. Diel B.N., Brandt P.F., Haltiwanger R.C., Hackney M.L.J., Norman A.D. Inorg. Chem. 1989, 28:2811.
74. Coles S.J., Edwards P.G., Fleming J.S., Hursthouse M.B. J. Chem. Soc., Dalton Trans. 1995, 1139.
75. Edwards P.G., Fleming J.S., Liyanage S.S., Coles S.J., Hursthouse M.B. J. Chem. Soc., Dalton Trans. 1996, 1801.
76. Edwards P.G., Fleming J.S., Liyanage S.S. J. Chem. Soc., Dalton Trans. 1997, 193.
77. Jones D.J., Edwards P.G., Tooze R.P., Albers T. J. Chem. Soc., Dalton Trans. 1999, 1045.
78. Edwards P.G., Newman P.D., Malik K.M.A. Angew. Chem., Int. Ed. 2000, 39:2922.
79. Edwards P.G., Haigh R., Li D., Newman P.D. J. Am. Chem. Soc. 2006, 128:3818.
80. Edwards P.G., Whatton M.L. Dalton Trans. 2006, 442.
81. Albers T., Edwards P.G. Chem. Commun. 2007, 858.
82. Price A.J., Edwards P.G. Chem. Commun. 2000, 899.
83. Edwards P.G., Newman P.D., Hibbs D.E. Angew. Chem. Int. Ed. 2000, 39:2722.
84. Battle A.R., Edwards P.G., Haigh R., Hibbs D.E., Li D., Liddiard S.M., Newman P.D. Organometallics 2007, 26:377.
85. Bauer E.B., Ruwwe J., Hampel F.A., Szafert S., Gladysz J.A., Martín-Alvarez J.M., Peters T.B., Bohling J.C., Lis T. Chem. Commun. 2000, 2261.
86. Driess M., Faulhaber M., Pritzkow H. Angew. Chem. Int. Ed. 1997, 36:1892.
87. Kaufhold O., Stasch A., Edwards P.G., Hahn F.E. Chem. Commun. 2007, 1822.
88. Kaufhold O., Stasch A., Pape T., Hepp A., Edwards P.G., Newman P.D., Hahn F.E. J. Am. Chem. Soc. 2009, 131:306.
89. Flores-Figueroa A., Kaufhold O., Hepp A., Froehlich R., Hahn F.E. Organometallics 2009, 28:6362.
90. DelDonno T.A., Rosen W. Inorg. Chem. 1978, 17:3714.
91. DelDonno T.A., Rosen W. J. Am. Chem. Soc. 1977, 99:8051.
92. Brauer D.J., Gol F., Hietkamp S., Peters H., Sommer H., Stelzer O., Sheldrick W.S. Chem. Ber. 1986, 119:349.
93. Baacke M., Stelzer O., Wray V. Chem. Ber. 1980, 113:1356.
94. Mizuta T., Okano A., Sasaki T., Nakazawa H., Miyoshi K. Inorg. Chem. 1997, 36:200.
95. Bartsch R., Hietkamp S., Morton S., Stelzer O. Angew. Chem. Int. Ed. 1982, 21:375.
96. Bartsch R., Hietkamp S., Morton S., Peters H., Stelzer O. Inorg. Chem. 1983, 22:3624.
97. Bartsch R., Hietkamp S., Peters H., Stelzer O. Inorg. Chem. 1984, 23:3304.
98. Brauer D.J., Lebbe T., Stelzer O. Angew. Chem. Int. Ed. 1988, 27:438.
99. Brauer D.J., Dörrenbach F., Lebbe T., Stelzer O. Chem. Ber. 1992, 125:1785.
100. Kang Y.B., Pabel M., Pathak D.D., Willis A.C., Wild S.B. Main Group Chem. 1995, 1:89.
101. Flores-Figueroa A., Pape T., Feldmann K.-O., Hahn F.E. Chem. Commun. 2010, 46:324.
102. Harnisch J.A., Angelici R.J. Inorg. Chim. Acta 2000, 300-302:273.
103. Baker R.J., Davies P.C., Edwards P.G., Farley R.D., Liyanage S.S., Murphy D.M., Yong B. Eur. J. Inorg. Chem. 2002, 1975.
104. Baker R.J., Edwards P.G., Gracia-Mora J., Ingold F., Abdul Malik K.M. J. Chem. Soc., Dalton Trans. 2002, 3985.
105. Ciampolini M., Dapporto P., Nicoletta N., Zanobini F. Inorg. Chem. 1983, 22:13.
106. Mercier F., Laporte F., Ricard L., Mathey F., Schröder M., Regitz M. Angew. Chem. Int. Ed. 1997, 36:2364.
107. Le Floch P., Mathey F. Coord. Chem. Rev. 1998, 178-180:771.
108. Mézailles N., Avarvari N., Maigrot N., Ricard L., Mathey F., Le Floch P., Cataldo L., Berclaz T., Geoffroy M. Angew. Chem. Int. Ed. 1999, 38:3194.
109. Mingos D.M.P. Pure Appl. Chem. 1980, 52:705.
110. Coles S.J., Edwards P.G., Fleming J.S., Hursthouse M.B. J. Chem. Soc., Dalton Trans. 1995, 4091.
111. Coles S.J., Edwards P.G., Fleming J.S., Hursthouse M.B., Liyanage S.S. Chem. Commun. 1996, 293.
112. Edwards P.G., Fleming J.S., Liyanage S.S. Inorg. Chem. 1996, 35:4563.