Synthesis of (porphinato)zinc(II)-spacer-(porphinato)iron(III) chloride complexes: A modular approach to fixed-distance electron-transfer model compounds through the efficacy of metal-mediated cross-coupling

Inorganica Chimica Acta

Volumn 242, Issue 1-2, 1996, Pages 211-218

  De Rege, Peter J F ^a   Therien, Michael J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

(Porphinato)iron complexes; (Porphinato)zinc complexes; Electron transfer; Pd catalyzed cross coupling

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; ELECTRON TRANSITIONS; IRON COMPOUNDS; MOLECULES; SHIMS; SYNTHESIS (CHEMICAL);

CROSS-COUPLINGS; DONOR SPACER ACCEPTORS; ELECTRON TRANSFER; IRON COMPLEX; MODULAR SYNTHESIS; REACTION SEQUENCES; SPACER MOLECULES; ZINC COMPLEX;

ZINC COMPOUNDS;

EID: 0007833593     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/0020-1693(95)04869-3     Document Type: Article

References (97)

1. (a) D.N. Beratan, J.N. Betts and J.N. Onuchic, Science (Washington DC), 252 (1991) 1285.
2. (b) J.N. Onuchic, D.N. Beratan, J.R. Winkler and H.B. Gray, Annu. Rev. Biophys. Biomol. Struct., 21 (1992) 349.
3. (c) J.N. Betts, D.N. Beratan and J.N. Onuchic, J. Am. Chem. Soc., 114 (1992) 4043.
4. (d) D.N. Beratan, J.N. Betts and J.N. Onuchic, J. Phys. Chem., 96 (1992) 2852.
5. (a) M.J. Therien, J. Chang, A.L. Raphael, B.E. Bowler and H.B. Gray, Structure and Bonding, 75 (1991) 109.
6. (b) J.R. Winkler and H.B. Gray, Chem. Rev., 92 (1992) 369.
7. (c) C.C. Moser, J.M. Keske, K. Warncke, R.S. Farid and P.L. Dutton, Nature (London), 355 (1992) 796.
8. (a) M.J. Therien, M.A. Selman, H.B. Gray, I.-J. Chang and J.R. Winkler, J. Am. Chem. Soc., 112 (1990) 2420.
9. (b) M.J. Therien, B.E. Bowler, M.A. Selman, H.B. Gray, I.-J. Chang and J.R. Winkler, Adv. Chem. Ser., 228 (1991) 191.
10. (a) D.S. Wuttke, M.J. Bjerrum, J.R. Winkler and H.B. Gray, Science (Washington DC), 256 (1992) 1007.
11. (b) D.N. Beratan, J.N. Onuchic, J.R. Winkler and H.B. Gray, Science (Washington DC), 258 (1992) 1740.
12. (c) H. Pelletier and J. Kraut, Science (Washington DC), 258 (1992) 1748.
13. (d) K.V. Mikkelsen, L.K. Skov, H. Nar and O. Farver, Proc. Natl. Acad. Sci. USA, 90 (1993) 5443.
14. C. Turró, C.K. Chang, G.E. Leroi, R.I. Cukier and D.G. Nocera, J. Am. Chem. Soc., 114 (1992) 4013.
15. (a) A. Harriman, D.J. Magda and J.L. Sessler, J. Phys. Chem., 95 (1991) 1530.
16. (b) A. Harriman, Y. Kubo and J.L. Sessler, J. Am. Chem. Soc., 114 (1992) 388.
17. (c) J.L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 115 (1993) 10418.
18. (a) M.R. Wasielewski, M.P. Niemczyk, W.A. Svec and E.B. Pewitt, J. Am. Chem. Soc., 107 (1985) 1080.
19. (b) A.D. Joran, B.A. Leland, P.M. Felker, A.H. Zewail, J.J. Hopfield and P.B. Dervan, Nature (London), 327 (1987) 508.
20. (c) G.L. Gaines, III, M.P. O'Neil, W.A. Svec, M.P. Niemczyk and M.R. Wasielewski, J. Am. Chem. Soc., 113 (1991) 719.
21. (a) R.L. Brookfield, H. Ellul and A. Harriman, J. Chem. Soc., Faraday Trans. 2, 81 (1985) 1837.
22. (b) N. Mataga, H. Yao, T. Okada, Y. Kanda and A. Harriman, Chem. Phys., 131 (1989) 473.
23. (c) A. Osuka, K. Maruyama, N. Mataga, T. Asahi, I. Yamazaki and N. Tamai, J. Am. Chem. Soc., 112 (1990) 4958.
24. A. Helms, D. Heiler and G. McLendon, J. Am. Chem. Soc., 114 (1992) 6227.
25. P.J.F. de Rege, S.A. Williams and M.J. Therien, Science (Washington DC), 269 (1995) 1409.
26. (a) F.R. Longo, M.G. Finarelli and J.B. Kim, J. Heterocylic. Chem., 6 (1968) 927.
27. (b) J.A. Anton and P.A. Loach, J. Heterocylic Chem., 12 (1975) 573.
28. (a) A.D. Adler, F.R. Longo, J.D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem., 32 (1967) 476.
29. (b) J.S. Lindsey, I.C. Schreiman, H.C. Hsu, P.C. Kearney and A.M. Marguerettaz, J. Org. Chem., 52 (1987) 827.
30. A. Osuka, F. Kobayashi, T. Nagata and K. Maruyama, Chem. Lett., (1990) 287.
31. (a) C.K. Chang and I. Abdalmuhdi, J. Org. Chem., 48 (1983) 5388.
32. (b) C.K. Chang and I. Abdalmuhdi, Angew. Chem. Int. Ed. Engl., 23 (1984) 164.
33. (c) S.S. Eaton, G.R. Eaton and C.K. Chang, J. Am. Chem. Soc., 107 (1985) 3177.
34. (d) J.P. Fillers, K.G. Ravichandran, I. Abdalmuhdi, A. Tulinsky and C.K. Chang, J. Am. Chem. Soc., 108 (1986) 417.
35. (e) J.L. Sessler, J. Hugdahl and M.R. Johnson, J. Org. Chem., 51 (1986) 2838.
36. (f) J.L. Sessler and M.R. Johnson, Angew. Chem. Int. Ed. Engl., 26 (1987) 678.
37. (g) J.L. Sessler and S. Piering, Tetrahedron Lett., 28 (1987) 6569.
38. (h) A. Osuka and K. Maruyama, J. Am. Chem. Soc., 110 (1988) 4454.
39. (i) A. Osuka, K. Maruyama, I. Yamazaki and N. Tamai, J. Chem. Soc., Chem. Commun. (1988) 1243-1245.
40. (j) A. Osuka, K. Ida and K. Maruyama, Chem. Lett., (1989) 741.
41. (k) K. Maruyama, T. Nagata, N. Ono and A. Osuka, Bull. Chem. Soc. Jpn., 62 (1989) 3167.
42. (l) J.L. Sessler, M.R. Johnson, S.E. Creager, J.C. Fettinger and J.A. Ibers, J. Am. Chem. Soc., 112 (1990) 9310.
43. (m) K. Maruyama and S. Kawabata, Bull. Chem. Soc. Jpn., 63 (1990) 170.
44. (n) J.P. Collman, J.E. Hutchison, M.A. Lopez, A. Tabard, R. Guilard, W.K. Seok, J.A. Ibers and M. L'Her, J. Am. Chem. Soc., 114 (1992) 9869.
45. (o) R. Guilard, M.A. Lopez, A. Tabard, P. Richard, C. Lecomte, S. Brandes, J.E. Hutchison and J.P. Collman, J. Am. Chem. Soc., 114 (1992) 9877.
46. J.L. Sessler, V.L. Capuano and A. Harriman, J. Am. Chem. Soc., 115 (1993) 4618.
47. (a) I. Abdalmuhdi and C.K. Chang, J. Org. Chem., 50 (1985) 411.
48. (b) A. Osuka, K. Ida, T. Nagata, K. Maruyama, I. Yamazaki, N. Tamai and Y. Nishimura, Chem. Lett. (1989) 2133.
49. (c) T. Nagata, A. Osuka and K. Maruyama, J. Am. Chem. Soc., 112 (1990) 3054.
50. (d) M.R. Wasielewski, D.G. Johnson, M.P. Niemczyk, G.L. Gaines, III, M.P. O'Neil and W.A. Svec, J. Am. Chem. Soc., 112 (1990) 6482.
51. (e) A. Osuka, F. Kobayashi and K. Maruyama, Chem. Lett. (1990) 1521.
52. (f) A. Osuka, F. Kobayashia and K. Maruyama, Bull. Chem. Soc. Jpn., 64 (1991) 1213.
53. (g) A. Osuka, T. Nagata and K. Maruyama, Chem. Lett. (1991) 481.
54. (h) A. Osuka, T. Nagata and K. Maruyama, Chem. Lett., (1991) 1687.
55. (i) A. Osuka, S. Nakajima and K. Maruyama, J. Org. Chem., 57 (1992) 7355.
56. (j) A. Osuka, F. Kobayashi, S. Nakajima, K. Maruyama, I. Yamazaki and Y. Nishimura, Chem. Lett., (1993) 161.
57. (k) A. Osuka, N. Tanabe, R.-P. Zhang and K. Maruyama, Chem. Lett, (1993) 1505.
58. A. Osuka, B.-I. Liu and K. Maruyama, J. Org. Chem., 58 (1993) 3582.
59. (m) A. Osuka, R.-P. Zhang, K. Maruyama, T. Ohno and K. Nozaki, Bull. Chem. Soc. Jpn., 66 (1993) 3773.
60. (n) A. Osuka, S. Nakajima, K. Maruyama, N. Mataga, T. Asahi, I. Yamazaki, Y. Nishimura, T. Ohno and K. Nozaki, J. Am. Chem. Soc., 115 (1993) 4577.
61. (o) S. Kawabata, N. Tanabe and A. Osuka, Chem. Lett., (1994) 1797.
62. R. Little, J. Heterocyclic Chem., 15 (1978) 203.
63. (a) J.P. Collman, C.M. Elliott, T.R. Halbert and B.S. Tovrog, Proc. Natl. Acad. Sci. USA, 74 (1977) 18.
64. (b) C.K. Chang, M.-S. Kuo and C.-B. Wang, J. Heterocyclic Chem., 14 (1977) 943.
65. (c) J.P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval and F.C. Anson, J. Am. Chem. Soc., 102 (1980) 6027.
66. (d) J.P. Collman, F.C. Anson, C.E. Barnes, C.S. Bencosme, T. Geiger, E.R. Evitt, R.P. Kreh, K. Meier and R.B. Pettman, J. Am. Chem. Soc., 105 (1983) 2694.
67. J.P. Collman, A.O. Chong, G.B. Jameson, R.T. Oakley, E. Rose, E.R. Schmittou and J.A. Ibers, J. Am. Chem. Soc., 103 (1981) 516.
68. A. Vidal-Ferran, C.M. Müller and J.K.M. Sanders, J. Chem. Soc., Chem. Commun., (1994) 2657.
69. (a) S. Prathapan, I.E. Johnson and J.S. Lindsey, J. Am. Chem. Soc., 115 (1993) 7519.
70. (b) J.S. Lindsey, S. Prathapan, T.E. Johnson and R.W. Wagner, Tetrahedron, 50 (1994) 8941.
71. (c) J. Seth, V. Palaniappan, T.E. Johnson, S. Prathapan, J.S. Lindsey and D.F. Bocian, J. Am. Chem. Soc., 116 (1994) 10578.
72. D.P. Arnold and L.J. Nitschinsk, Tetrahedron Lett., 34 (1993) 693.
73. (a) H.L. Anderson and J.K.M. Sanders, J. Chem. Soc., Chem. Commun., (1989) 1714.
74. (b) H.L. Anderson and J.K.M. Sanders, Angew. Chem. Int. Ed. Engl., 29 (1990) 1400.
75. (c) D.P. Arnold and L.J. Nitschinsk, Tetrahedron, 48 (1992) 8781.
76. (d) H.L. Anderson, S.J. Martin and D.D.C. Bradley, Angew. Chem. Int. Ed. Engl., 33 (1994) 655.
77. (e) H.L. Anderson, Inorg. Chem., 33 (1994) 972.
78. (f) J.J. Gosper and M. Ali, J. Chem. Soc. Chem. Commun., (1994) 1707.
79. (g) D.P. Arnold, D.A. James, C.H.L. Kennard and G. Smith, J. Chem. Soc., Chem. Commun., (1994) 2131.
80. (h) H. Imahori, H. Higuchi, Y. Matsuda, A. Itagaki, Y. Sakai, J. Ojima and Y. Sakata, Bull. Chem. Soc. Jpn., 67 (1994) 2500.
81. M.J. Crossley and P.L. Burn, J. Chem. Soc. Chem. Commun., (1991) 1569.
82. M.P. O'Neil, M.P. Niemczyk, W.A. Svec, D. Gosztola, G.L. Gaines, III and M.R. Wasielewski, Science (Washington, DC), 257 (1992) 63.
83. G.V. Ponomarev, V.V. Borovkov, K.-i. Sugiura, Y. Sakata and A.M. Shul'ga, Tetrahedron Lett., 34 (1993) 2153.
84. (a) M. Kumada, Pure Appl. Chem., 52 (1980) 669.
85. (b) E.-I. Negishi, F.T. Luo, R. Frisbee and H. Matsushita, Heterocycles, 18 (1982) 117.
86. (c) R.F. Heck, Ace. Chem. Res., 12 (1979) 146.
87. (d) J.K. Stille, Agnew. Chem., Int. Ed. Engl., 25 (1986) 508-524.
88. (a) S.G. DiMagno, V.S.-Y. Lin and M.J. Therien, J. Am Chem. Soc., 115 (1993) 2513.
89. (b) S.G. DiMagno, V.S.-Y. Lin and M.J. Therien, J. Org. Chem., 58 (1993) 5983.
90. (a) V.S.-Y. Lin, S.G. DiMagno and M.J. Therien, Science (Washington, DC), 264 (1994) 1105.
91. (b) V.S.-Y. Lin and M.J. Therien, Chem. Eur. J., 1 (1995) 645.
92. X. Zhou and K.S. Chan, J. Chem. Soc., Chem. Commun., (1994) 2493.
93. M. Hudlicky, Reductions in Organic Chemistry, Ellis Howard, West Sussex, 1984, p. 79.
94. (a) A.L. Henne and W.F. Zimmer, J. Am. Chem. Soc., 73 (1951) 1362.
95. (b) R.N. Haszeldine and A.G. Sharpe, J. Chem. Soc., 73 (1952) 993.
96. J.K.M. Sanders and B.K. Hunter, Modern NMR Spectroscopy: A Guide for Chemists, Oxford University Press, Oxford, 1987, pp. 163-207.
97. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi and K. Hirotsu, J. Am. Chem. Soc., 106 (1984) 158.