Invited review. A combinatorial approach to the development of environmentally benign organic chemical preparations

Australian Journal of Chemistry

Volumn 52, Issue 2, 1999, Pages 83-96

  Strauss, Christopher R ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003031056     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/C98156     Document Type: Article

References (181)

1. Haggin, J., Chem. Eng. News, 1996, 74(23), 38.
2. Eigenmann, K., Chimia, 1997, 51, 169, and papers in that issue, pp. 171-232.
3. Casumano, J. A., J. Chem. Educ., 1995, 72, 959.
4. Collins, T. J., J. Chem. Educ., 1995, 72, 965.
5. Swan, J. A., and Spiro, T. G., J. Chem. Educ., 1995, 72, 967.
6. Tebo, P. V., CHEMTECH, 1998, 28(3), 8.
7. Weiner, S. C., Cranford, B., and Chum, H., CHEMTECH, 1998, 28(4), 10, and references cited therein.
8. Hildebrandt, B.-U., and Schlottmann, U., Angew. Chem., Int. Ed. Engl., 1998, 37, 1316.
9. Kirschner, E. M., Chem. Eng. News, 1994, 72(25), 13.
10. Willis, L., CHEMTECH, 1998, 28(8), 18.
11. Illman, D. L., Chem. Eng. News, 1994, 72(36), 22.
12. Trogler, W. C., J. Chem. Educ., 1995, 72, 973.
13. Sidebottom, H., and Franklin, J., Pure Appl. Chem., 1996, 68, 1757.
14. Key, B. D., Howell, R. D., and Criddle, C. S., Environ. Sci. Technol., 1997, 31, 2445.
15. Pereira, S. M., Savage, G. P., and Simpson, G. W., Synth. Commun., 1995, 25, 1023.
16. Katritzky, A. R., Toader, D., and Jiang, J., Org. Prep. Proced. Int., 1995, 27, 179.
17. Kanegsberg, B., Chem. Ind. (London), 1996, 787.
18. DeVito, S. C., CHEMTECH, 1996, 26(11), 34.
19. Elango, N., Murphy, M. A., Smith, B. L., Davenport, K. G., Mott, G. N., and Moss, G. L., Eur. Pat. Appl. 0284310 (1988).
20. Hitzler, M. G., Smail, F. R., Ross, S. K., and Poliakoff, M., Chem. Commun., 1998, 359.
21. Fache, F., Bethmont, V., Jacquot, L., and Lemaire, M., Recl Trav. Chim. Pays-Bas, 1996, 115, 231.
22. Smith, K., Musson, A., and DeBoos, G. A., Chem. Commun., 1996, 469.
23. Clark, J. H., Martin, K., Teasdale, A. J., and Barlow, S. J., J. Chem. Soc., Chem. Commun., 1995, 2037.
24. Butterworth, A. J., Clark, J. H., Walton, P. H., and Barlow, S. J., Chem. Commun., 1996, 1859.
25. Clark, J. H., Ross, J. C., Macquarrie, D. J., Barlow, S. J., and Bastock, T. W., Chem. Commun., 1997, 1203.
26. Hinzen, B., and Ley, S. V., J. Chem. Soc., Perkin Trans. 1, 1997, 1907.
27. Clark, J. H., Price, P. M., Martin, K., Macquarrie, D. J., and Bastock, T. W., J. Chem. Res. (S), 1997, 430.
28. Kobayashi, S., Pure Appl. Chem., 1998, 70, 1019.
29. Kobayashi, S., Araki, M., and Hachiya, I., J. Org. Chem., 1994, 59, 3758.
30. Kobayashi, S., and Hachiya, I., J. Org. Chem., 1994, 59, 3590.
31. Kobayashi, S., and Ishitani, H., J. Chem. Soc., Chem. Commun., 1995, 1379.
32. Ishihara, K., Kubota, M., Kurihara, H., and Yamamoto, H., J. Org. Chem., 1996, 61, 4560.
33. Olah, G. A., Prakash, G. K. S., and Sommer, J., 'Superacids' (John Wiley: New York 1985).
34. Olah, G. A., Iyer, P. S., and Prakash, G. K. S., Synthesis, 1986, 513.
35. Kobayashi, S., and Nagayama, S., J. Org. Chem., 1996, 61, 2256.
36. Olah, G. A., Chem. Br., 1996, No. 8, 21; Smith, K., Chem. Br., 1996, No. 8, 21.
37. Olah, G. A., Chem. Br., 1996, No. 8, 21; Smith, K., Chem. Br., 1996, No. 8, 21.
38. Sheldon, R. A., Chem. Ind. (London), 1997, 12, and references cited therein.
39. Trost, B. M., Science, 1991, 254, 1471.
40. Trost, B. M., Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
41. Lester, T., Chem. Br., 1996, No. 12, 45.
42. Sheldon, R. A., CHEMTECH, 1994, 24(3), 38.
43. Sheldon, R. A., Chem. Ind. (London), 1992, 903.
44. Clark, J. H., and Macquarrie, D. J., Chem. Soc. Rev., 1996, 25, 303.
45. Clark, J. H., and Macquarrie, D., Org. Process Res. Dev., 1997, 1, 149.
46. Clark, J. H., and Macquarrie, D., Chem. Commun., 1998, 853.
47. Szmant, H. H., 'Organic Building Blocks of the Chemical Industry' (a) Gh. 9, pp. 503-505; (b) Ch. 2, pp. 29-57 (John Wiley: New York 1989).
48. Szmant, H. H., 'Organic Building Blocks of the Chemical Industry' (a) Gh. 9, pp. 503-505; (b) Ch. 2, pp. 29-57 (John Wiley: New York 1989).
49. Kent, J. A., (Ed.) "Riegel's Handbook of Industrial Chemistry" Ch. 1, pp. 1-13, and Ch. 18, p. 648 (Van Nostrand Reinhold: New York 1983).
50. Kent, J. A., (Ed.) "Riegel's Handbook of Industrial Chemistry" Ch. 1, pp. 1-13, and Ch. 18, p. 648 (Van Nostrand Reinhold: New York 1983).
51. Curran, D. P., Angew. Chem., Int. Ed. Engl., 1998, 37, 1174.
52. Cablewski, T., Faux, A. F., and Strauss, C. R., J. Org. Chem., 1994, 59, 3408.
53. Strauss, C. R., and Faux, A. F., U.S. Pat. 5,387,397 (1995).
54. Strauss, C. R., and Faux, A. F., Eur. Pat. 0437480 (1994).
55. Raner, K. D., Strauss, C. R., Trainor, R. W., and Thorn, J. S., J. Org. Chem., 1995, 60, 2456.
56. Strauss, C. R., Raner, K. D., Trainor, R. W., and Thorn, J. S., Aust. Pat. 677876 (1997), and other applications pending.
57. Li, J., Mau, A. W.-H., and Strauss, C. R., Chem. Commun., 1997, 1275.
58. Cablewski, T., Gurr, P. A., Pajalic, P. J., and Strauss, C. R., unpublished data.
59. Cablewski, T., Gurr, P. A., Raner, K. D., and Strauss, C. R., J. Org. Chem., 1994, 59, 5814.
60. Strauss, C. R., and Trainor R. W., Org. Prep. Proced. Int., 1995, 27, 552.
61. Strauss, C. R., and Trainor, R. W., Aust. J. Chem., 1998, 51, 703.
62. Bagnell, L., Cablewski, T., and Strauss, C. R., Chem. Commun., in press. A patent application has been filed.
63. Bagnell, L., and Strauss, C. R., Chem. Commun., in press. A patent application has been filed.
64. Bagnell, L., Cablewski, T., Strauss, C. R., and Trainor, R. W., J. Org. Chem., 1996, 61, 7355, and references cited therein.
65. An, J., Bagnell, L., Cablewski, T., Strauss, C. R., and Trainor, R. W., J. Org. Chem., 1997, 62, 2505, and references cited therein.
66. Bagnell, L., Bliese, M., Cablewski, T., Strauss, C. R., and Tsanaktsidis, J., Aust. J. Chem., 1997, 50, 921.
67. Fruchtel, J. S., and Jung, G., Angew. Chem., Int. Ed. Engl., 1996, 35, 17; Bailey, N., Cooper, A. W. J., Deal, M. J., Dean, A. W., Gore, A. L., Hawes, M. C., Judd, D. B., Merritt, A. T., Storer, R., Travers, S., and Watson, S. P., Chimia, 1997, 51, 832; Brown, A. R., Hermkens, P. H. H., Ottenheijm, H. C. J., and Rees, D. C., Synlett, 1998, 817; Loughlin, W. A., Aust. J. Chem., 1998, 51, 875.
68. Fruchtel, J. S., and Jung, G., Angew. Chem., Int. Ed. Engl., 1996, 35, 17; Bailey, N., Cooper, A. W. J., Deal, M. J., Dean, A. W., Gore, A. L., Hawes, M. C., Judd, D. B., Merritt, A. T., Storer, R., Travers, S., and Watson, S. P., Chimia, 1997, 51, 832; Brown, A. R., Hermkens, P. H. H., Ottenheijm, H. C. J., and Rees, D. C., Synlett, 1998, 817; Loughlin, W. A., Aust. J. Chem., 1998, 51, 875.
69. Fruchtel, J. S., and Jung, G., Angew. Chem., Int. Ed. Engl., 1996, 35, 17; Bailey, N., Cooper, A. W. J., Deal, M. J., Dean, A. W., Gore, A. L., Hawes, M. C., Judd, D. B., Merritt, A. T., Storer, R., Travers, S., and Watson, S. P., Chimia, 1997, 51, 832; Brown, A. R., Hermkens, P. H. H., Ottenheijm, H. C. J., and Rees, D. C., Synlett, 1998, 817; Loughlin, W. A., Aust. J. Chem., 1998, 51, 875.
70. Fruchtel, J. S., and Jung, G., Angew. Chem., Int. Ed. Engl., 1996, 35, 17; Bailey, N., Cooper, A. W. J., Deal, M. J., Dean, A. W., Gore, A. L., Hawes, M. C., Judd, D. B., Merritt, A. T., Storer, R., Travers, S., and Watson, S. P., Chimia, 1997, 51, 832; Brown, A. R., Hermkens, P. H. H., Ottenheijm, H. C. J., and Rees, D. C., Synlett, 1998, 817; Loughlin, W. A., Aust. J. Chem., 1998, 51, 875.
71. See the review: Strauss, C. R., and Trainor, R. W., Aust. J. Chem., 1995, 48, 1665.
72. Schillmoller, C. M., in 'Encyclopedia of Chemical Processing and Design' (Eds J. J. McKetta and W. A. Cunningham) Vol. 31, pp. 80-87 (Marcel Dekker: New York 1990).
73. Kontoghiorghes, G. J., and Sheppard, L., Inorg. Chim. Acta, 1987, 136, L11.
74. Anon., Drugs Future, 1996, 21, 543; Singh, S., Chem. Ind. (London), 1994, 452.
75. Anon., Drugs Future, 1996, 21, 543; Singh, S., Chem. Ind. (London), 1994, 452.
76. Haggin, J., Chem. Eng. News, 1994, 72(2), 22; Wan, J. K. S., and Koch, T. A., Res. Chem. Intermed., 1994, 20, 29; Mehdizadeh, M., Res. Chem. Intermed., 1994, 20, 79.
77. Haggin, J., Chem. Eng. News, 1994, 72(2), 22; Wan, J. K. S., and Koch, T. A., Res. Chem. Intermed., 1994, 20, 29; Mehdizadeh, M., Res. Chem. Intermed., 1994, 20, 79.
78. Haggin, J., Chem. Eng. News, 1994, 72(2), 22; Wan, J. K. S., and Koch, T. A., Res. Chem. Intermed., 1994, 20, 29; Mehdizadeh, M., Res. Chem. Intermed., 1994, 20, 79.
79. Siskin, M., and Katritzky, A. R., Science, 1991, 254, 231.
80. Katritzky, A. R., Allin, S. M., and Siskin, M., Acc. Chem. Res., 1996, 29, 399.
81. Parsons, E. J., CHEMTECH, 1996, 26(7), 30, and references therein.
82. Kuhlmann, B., Arnett, E. M., and Siskin, M., J. Org. Chem., 1994, 59, 3098.
83. Kuhlmann, B., Arnett, E. M., and Siskin, M., J. Org. Chem., 1994, 59, 5377.
84. Sealock, L. J., Elliott, D. G., Baker, E. G., and Butner, R. S., Ind. Eng. Chem. Res., 1993, 32, 1535.
85. Robinson, B., 'The Fischer Indole Synthesis' (a) p. 401; (b) p. xi; p. 393; p. 399 (John Wiley: Chichester 1982).
86. Robinson, B., 'The Fischer Indole Synthesis' (a) p. 401; (b) p. xi; p. 393; p. 399 (John Wiley: Chichester 1982).
87. Robinson, B., 'The Fischer Indole Synthesis' (a) p. 401; (b) p. xi; p. 393; p. 399 (John Wiley: Chichester 1982).
88. Robinson, B., 'The Fischer Indole Synthesis' (a) p. 401; (b) p. xi; p. 393; p. 399 (John Wiley: Chichester 1982).
89. Hanson, D. J., Chem. Eng. News, 1998, 76(27), 19.
90. Okochi, H., Kajimoto, T., Arai, Y., and Igawa, M., Bull. Chem. Soc. Jpn, 1996, 69, 3355.
91. Acheson, R. M., and Robinson, R., J. Chem. Soc., 1952, 1127; Vogel, A. I., 'Practical Organic Chemistry' 4th Edn, p. 854 (Longmans: New York 1978); Karpinski, M. L., Nicholas, D., and Gilbert, J. C., Org. Prep. Proced. Int., 1995, 27, 569.
92. Acheson, R. M., and Robinson, R., J. Chem. Soc., 1952, 1127; Vogel, A. I., 'Practical Organic Chemistry' 4th Edn, p. 854 (Longmans: New York 1978); Karpinski, M. L., Nicholas, D., and Gilbert, J. C., Org. Prep. Proced. Int., 1995, 27, 569.
93. Acheson, R. M., and Robinson, R., J. Chem. Soc., 1952, 1127; Vogel, A. I., 'Practical Organic Chemistry' 4th Edn, p. 854 (Longmans: New York 1978); Karpinski, M. L., Nicholas, D., and Gilbert, J. C., Org. Prep. Proced. Int., 1995, 27, 569.
94. Katritzky, A. R., Luxem, F. J., and Siskin, M., Energy Fuels, 1990, 4, 518.
95. For reviews, see: Li, C.-J., Tetrahedron, 1996, 52, 5643; Li, C.-J., Chem. Rev., 1993, 93, 2023; Pindur, U., Lutz, G., and Otto, C., Chem. Rev., 1993, 93, 741; Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741; Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
96. For reviews, see: Li, C.-J., Tetrahedron, 1996, 52, 5643; Li, C.-J., Chem. Rev., 1993, 93, 2023; Pindur, U., Lutz, G., and Otto, C., Chem. Rev., 1993, 93, 741; Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741; Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
97. For reviews, see: Li, C.-J., Tetrahedron, 1996, 52, 5643; Li, C.-J., Chem. Rev., 1993, 93, 2023; Pindur, U., Lutz, G., and Otto, C., Chem. Rev., 1993, 93, 741; Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741; Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
98. For reviews, see: Li, C.-J., Tetrahedron, 1996, 52, 5643; Li, C.-J., Chem. Rev., 1993, 93, 2023; Pindur, U., Lutz, G., and Otto, C., Chem. Rev., 1993, 93, 741; Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741; Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
99. For reviews, see: Li, C.-J., Tetrahedron, 1996, 52, 5643; Li, C.-J., Chem. Rev., 1993, 93, 2023; Pindur, U., Lutz, G., and Otto, C., Chem. Rev., 1993, 93, 741; Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741; Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
100. Williams, P. J., Strauss, C. R., Wilson, B., and Massy-Westropp, R. A., J. Chromatogr., 1982, 235, 471; Gunata, Y. Z., Bayonove, C. L., Baumes, R. L., and Cordonnier, R. E., J. Chromatogr., 1985, 331, 83; Matthews, R. F., Rouseff, R. L., Manlan, M., and Norman, S. I., Food Technol., 1990, 44(4), 130; Tseng, D. J., Matthews, R. F., Gregory, J. F., Wei, C. I., and Littel, R. C., J. Food Sci., 1993, 58, 801; Ericson, A. P., Matthews, R. F., Teixeira, A. A., and Moye, H. A., J. Food Sci., 1992, 57, 186.
101. Williams, P. J., Strauss, C. R., Wilson, B., and Massy-Westropp, R. A., J. Chromatogr., 1982, 235, 471; Gunata, Y. Z., Bayonove, C. L., Baumes, R. L., and Cordonnier, R. E., J. Chromatogr., 1985, 331, 83; Matthews, R. F., Rouseff, R. L., Manlan, M., and Norman, S. I., Food Technol., 1990, 44(4), 130; Tseng, D. J., Matthews, R. F., Gregory, J. F., Wei, C. I., and Littel, R. C., J. Food Sci., 1993, 58, 801; Ericson, A. P., Matthews, R. F., Teixeira, A. A., and Moye, H. A., J. Food Sci., 1992, 57, 186.
102. Williams, P. J., Strauss, C. R., Wilson, B., and Massy-Westropp, R. A., J. Chromatogr., 1982, 235, 471; Gunata, Y. Z., Bayonove, C. L., Baumes, R. L., and Cordonnier, R. E., J. Chromatogr., 1985, 331, 83; Matthews, R. F., Rouseff, R. L., Manlan, M., and Norman, S. I., Food Technol., 1990, 44(4), 130; Tseng, D. J., Matthews, R. F., Gregory, J. F., Wei, C. I., and Littel, R. C., J. Food Sci., 1993, 58, 801; Ericson, A. P., Matthews, R. F., Teixeira, A. A., and Moye, H. A., J. Food Sci., 1992, 57, 186.
103. Williams, P. J., Strauss, C. R., Wilson, B., and Massy-Westropp, R. A., J. Chromatogr., 1982, 235, 471; Gunata, Y. Z., Bayonove, C. L., Baumes, R. L., and Cordonnier, R. E., J. Chromatogr., 1985, 331, 83; Matthews, R. F., Rouseff, R. L., Manlan, M., and Norman, S. I., Food Technol., 1990, 44(4), 130; Tseng, D. J., Matthews, R. F., Gregory, J. F., Wei, C. I., and Littel, R. C., J. Food Sci., 1993, 58, 801; Ericson, A. P., Matthews, R. F., Teixeira, A. A., and Moye, H. A., J. Food Sci., 1992, 57, 186.
104. Williams, P. J., Strauss, C. R., Wilson, B., and Massy-Westropp, R. A., J. Chromatogr., 1982, 235, 471; Gunata, Y. Z., Bayonove, C. L., Baumes, R. L., and Cordonnier, R. E., J. Chromatogr., 1985, 331, 83; Matthews, R. F., Rouseff, R. L., Manlan, M., and Norman, S. I., Food Technol., 1990, 44(4), 130; Tseng, D. J., Matthews, R. F., Gregory, J. F., Wei, C. I., and Littel, R. C., J. Food Sci., 1993, 58, 801; Ericson, A. P., Matthews, R. F., Teixeira, A. A., and Moye, H. A., J. Food Sci., 1992, 57, 186.
105. Williams, P. J., and Strauss, C. R., J. Sci. Food Agric., 1978, 29, 527.
106. Williams, P. J., Strauss, C. R., Klingner, K. E., Obst, S. R., and Anderson, G. L. G., Food Technol. Aust., 1981, 33, 12.
107. Zamaraev, K. I., Pure Appl. Chem., 1996, 68, 357, and references therein.
108. Hegedus, L. S., Tetrahedron, 1984, 40, 2415; Heck, R. F., Org. React., 1982, 27, 345; Heck, R. F., 'Palladium Reagents in Organic Chemistry' (Academic: London 1985).
109. Hegedus, L. S., Tetrahedron, 1984, 40, 2415; Heck, R. F., Org. React., 1982, 27, 345; Heck, R. F., 'Palladium Reagents in Organic Chemistry' (Academic: London 1985).
110. Hegedus, L. S., Tetrahedron, 1984, 40, 2415; Heck, R. F., Org. React., 1982, 27, 345; Heck, R. F., 'Palladium Reagents in Organic Chemistry' (Academic: London 1985).
111. de Meijere, A., and Meyer, F. E., Angew. Chem., Int. Ed. Engl., 1994, 33, 2379; Heck, R. F., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 4 (Ed. M. F. Semmelhack) p. 833 (Pergamon: Oxford 1993).
112. de Meijere, A., and Meyer, F. E., Angew. Chem., Int. Ed. Engl., 1994, 33, 2379; Heck, R. F., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 4 (Ed. M. F. Semmelhack) p. 833 (Pergamon: Oxford 1993).
113. Beller, M., and Riermeier, T. H., Tetrahedron Lett., 1996, 37, 6535; Herrmann, W. A., Reisinger, C.-P., Ofele, K., Brossmer, C., Beller, M., and Fischer, H., J. Mol. Catal. A: Chem., 1996, 108, 51.
114. Beller, M., and Riermeier, T. H., Tetrahedron Lett., 1996, 37, 6535; Herrmann, W. A., Reisinger, C.-P., Ofele, K., Brossmer, C., Beller, M., and Fischer, H., J. Mol. Catal. A: Chem., 1996, 108, 51.
115. Kiviaho, J., Hanaoka, T., Kubota, Y., and Sugi, Y., J. Mol. Catal. A: Chem., 1995, 101, 25.
116. Cornils, B., Angew. Chem., Int. Ed. Engl., 1995, 34, 1575; Cornils, B., Org. Proc. Res. Dev., 1998, 2, 121.
117. Cornils, B., Angew. Chem., Int. Ed. Engl., 1995, 34, 1575; Cornils, B., Org. Proc. Res. Dev., 1998, 2, 121.
118. Melpolder, J. B., and Heck, R. F., J. Org. Chem., 1976, 41, 265; Dyker, G., and Grundt, P., Tetrahedron Lett., 1996, 37, 619, and references therein.
119. Melpolder, J. B., and Heck, R. F., J. Org. Chem., 1976, 41, 265; Dyker, G., and Grundt, P., Tetrahedron Lett., 1996, 37, 619, and references therein.
120. Theissen, R. J., J. Org. Chem., 1971, 36, 752.
121. Kaneda, K., Fujie, Y., and Ebitani, K., Tetrahedron Lett., 1997, 38, 9023.
122. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
123. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
124. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
125. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
126. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
127. Sonogashira, K., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 3 (Ed. G. Pattenden) p. 551 (Pergamon: Oxford 1993); Sakamoto, T., Nagata, H., Kondo, Y., Shiraiwa, M., and Yamanaka, H., Chem. Pharm. Bull., 1987, 35, 823; Vidal-Ferran, A., Muller, C. M., and Sanders, J. K. M., J. Chem. Soc., Chem. Commun., 1994, 2657; Melissaris, A. P., and Litt, M. H., J. Org. Chem., 1994, 59, 5818; Cassar, L., J. Organomet. Chem., 1975, 93, 253; Dieck, H. A., and Heck, R. F., J. Organomet. Chem., 1975, 93, 259.
128. Tonks, L., Anson, M. S., Hellgardt, K., Mirza, A. R., Thompson, D. F., and Williams, J. M. J., Tetrahedron Lett., 1997, 38, 4319.
129. Larhed, M., and Hallberg, A., J. Org. Chem., 1996, 61, 9582.
130. Bumagin, N. A., More, P. G., and Beletskaya, I. P., J. Organomet. Chem., 1989, 371, 397; Genet, J. P., Blart, E., and Savignac, M., Synlett, 1992, 715.
131. Bumagin, N. A., More, P. G., and Beletskaya, I. P., J. Organomet. Chem., 1989, 371, 397; Genet, J. P., Blart, E., and Savignac, M., Synlett, 1992, 715.
132. Reviewed by Feuer, H., and Hooz, J., in 'The Chemistry of the Ether Linkage' (Ed. S. Patai) Ch. 10, pp. 445-498 (Interscience: London 1967); Baggett, N., in 'Comprehensive Organic Chemistry' (Ser. Eds D. Barton and W. D. Ollis; Vol. Ed. J. F. Stoddart) Ch. 4.3, pp. 799-852 (Pergamon: Oxford 1979).
133. Reviewed by Feuer, H., and Hooz, J., in 'The Chemistry of the Ether Linkage' (Ed. S. Patai) Ch. 10, pp. 445-498 (Interscience: London 1967); Baggett, N., in 'Comprehensive Organic Chemistry' (Ser. Eds D. Barton and W. D. Ollis; Vol. Ed. J. F. Stoddart) Ch. 4.3, pp. 799-852 (Pergamon: Oxford 1979).
134. Mitsunobu, O., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 6 (Ed. E. Winterfeldt) pp. 1-31 (Pergamon: New York 1991).
135. Reviewed by Staude, E., and Patat, F., in 'The Chemistry of the Ether Linkage' (Ed. S. Patai) Ch. 2, pp. 21-80 (Interscience: London 1967).
136. Albrecht, R., Prog. Drug Res., 1977, 21, 9.
137. Gould, R. G., and Jacobs, W. A., J. Am. Chem. Soc., 1939, 61, 2890.
138. Price, C. C., and Roberts, R. M., J. Am. Chem. Soc., 1946, 68, 1204.
139. Danziger, W. J., in 'Kirk-Othmer Encyclopedia of Chemical Technology' 2nd Edn, Vol. 10, p. 846 (John Wiley: New York 1966).
140. Krieger, J., Chem. Eng. News, 1991, 69(51), 17.
141. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
142. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
143. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
144. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
145. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
146. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
147. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
148. For example: Pipaud, A., Rocher, R., and Chenault, J., Synth. Commun., 1997, 27, 1927; Heleyova, K., Ilavsky, D., Bobosik, V., and Pronayova, N., Collect. Czech. Chem. Commun., 1996, 61, 371; Heleyova, K., and Ilavsky, D., Collect. Czech. Chem. Commun., 1997, 62, 99; Richardson, T. O., Neale, N., and Carwell, N., J. Heterocycl. Chem., 1995, 32, 359; Uchida, M., Otsubo, K., Matsubara, J., Ohtani, T., Morita, S., and Yamasaki, K., Chem. Pharm. Bull., 1995, 43, 693; Heber, D., Ravens, U., and Schulze, T., Pharmazie, 1993, 48, 509; Abdalla, G. M., and Sowell, J. W., J. Heterocycl. Chem., 1990, 27, 1201; Carretero, J. C., Garcia Ruano, J. L., and Vicioso, M., Tetrahedron, 1992, 48, 7373.
149. Hermecz, I., Vasvari-Debreczy, L., Podanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 1998, 48, 1111; Grohe, K., Chem. Ber., 1993, 34; Jackson, A., and Meth-Cohn, O., J. Chem. Soc., Chem. Commun., 1995, 1319; Mitscher, L. A., Zavod, R. M., Devasthale, P. V., Chu, D. T. W., Shen, L. L., Sharma, P. N., and Pernet, A. G., CHEMTECH, 1991, 21(4), 249, and references cited therein; Dax, S. L., and Wei, C.-C., J. Org. Chem., 1992, 57, 744.
150. Hermecz, I., Vasvari-Debreczy, L., Podanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 1998, 48, 1111; Grohe, K., Chem. Ber., 1993, 34; Jackson, A., and Meth-Cohn, O., J. Chem. Soc., Chem. Commun., 1995, 1319; Mitscher, L. A., Zavod, R. M., Devasthale, P. V., Chu, D. T. W., Shen, L. L., Sharma, P. N., and Pernet, A. G., CHEMTECH, 1991, 21(4), 249, and references cited therein; Dax, S. L., and Wei, C.-C., J. Org. Chem., 1992, 57, 744.
151. Hermecz, I., Vasvari-Debreczy, L., Podanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 1998, 48, 1111; Grohe, K., Chem. Ber., 1993, 34; Jackson, A., and Meth-Cohn, O., J. Chem. Soc., Chem. Commun., 1995, 1319; Mitscher, L. A., Zavod, R. M., Devasthale, P. V., Chu, D. T. W., Shen, L. L., Sharma, P. N., and Pernet, A. G., CHEMTECH, 1991, 21(4), 249, and references cited therein; Dax, S. L., and Wei, C.-C., J. Org. Chem., 1992, 57, 744.
152. Hermecz, I., Vasvari-Debreczy, L., Podanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 1998, 48, 1111; Grohe, K., Chem. Ber., 1993, 34; Jackson, A., and Meth-Cohn, O., J. Chem. Soc., Chem. Commun., 1995, 1319; Mitscher, L. A., Zavod, R. M., Devasthale, P. V., Chu, D. T. W., Shen, L. L., Sharma, P. N., and Pernet, A. G., CHEMTECH, 1991, 21(4), 249, and references cited therein; Dax, S. L., and Wei, C.-C., J. Org. Chem., 1992, 57, 744.
153. Hermecz, I., Vasvari-Debreczy, L., Podanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 1998, 48, 1111; Grohe, K., Chem. Ber., 1993, 34; Jackson, A., and Meth-Cohn, O., J. Chem. Soc., Chem. Commun., 1995, 1319; Mitscher, L. A., Zavod, R. M., Devasthale, P. V., Chu, D. T. W., Shen, L. L., Sharma, P. N., and Pernet, A. G., CHEMTECH, 1991, 21(4), 249, and references cited therein; Dax, S. L., and Wei, C.-C., J. Org. Chem., 1992, 57, 744.
154. Brown, E. V., Synthesis, 1975, 358.
155. Wender, P. A., Chem. Rev., 1996, 96, 1.
156. Wender, P. A., Handy, S. T., and Wright, D. L., Chem. Ind. (London), 1997, 765.
157. For a definition, see Tietze, L. F., Chem. Rev., 1996, 96, 115.
158. For a definition, see Ho, T.-L., 'Tandem Organic Reactions' p. 1 (John Wiley: New York 1992).
159. For example: Wassmundt, F. W., and Padegimas, S. J., J. Am. Chem. Soc., 1967, 89, 7131; March, J., and Engenito, J. S., J. Org. Chem., 1981, 46, 4304; Nahmed, E. M., and Jenner, G., Tetrahedron Lett., 1991, 32, 4917.
160. For example: Wassmundt, F. W., and Padegimas, S. J., J. Am. Chem. Soc., 1967, 89, 7131; March, J., and Engenito, J. S., J. Org. Chem., 1981, 46, 4304; Nahmed, E. M., and Jenner, G., Tetrahedron Lett., 1991, 32, 4917.
161. For example: Wassmundt, F. W., and Padegimas, S. J., J. Am. Chem. Soc., 1967, 89, 7131; March, J., and Engenito, J. S., J. Org. Chem., 1981, 46, 4304; Nahmed, E. M., and Jenner, G., Tetrahedron Lett., 1991, 32, 4917.
162. For a review on methods of amidation see Beckwith, A. L. J., in 'The Chemistry of Amides' (Ed. J. Zabicky) p. 73 (Interscience: London 1970).
163. Erickson, D., Sci. Am., 1991 (August), 86.
164. Davenport, K. G., and Hilton, C. B., U.S. Pat. 4,560,789 (1985); Horlenko, T., and George, J. H., U.S. Pat. 4,665,216 (1987).
165. Davenport, K. G., and Hilton, C. B., U.S. Pat. 4,560,789 (1985); Horlenko, T., and George, J. H., U.S. Pat. 4,665,216 (1987).
166. Glauser, M., and Muller, P., Chimia, 1997, 51, 201.
167. Harmer, M. A., Sun, Q., Michalczyk, M. J., and Yang, Z., Chem. Commun., 1997, 1803.
168. For classification see: Braude, E. A., and Linstead, R. P., J. Chem. Soc., 1954, 3544.
169. For reviews on catalytic transfer hydrogenation, see: Brieger, G., and Nestrick, T. J., Chem. Rev., 1974, 74, 567; Johnstone, R. A. W., Wilby, A. H., and Entwistle, I. D., Chem. Rev., 1985, 85, 129.
170. For reviews on catalytic transfer hydrogenation, see: Brieger, G., and Nestrick, T. J., Chem. Rev., 1974, 74, 567; Johnstone, R. A. W., Wilby, A. H., and Entwistle, I. D., Chem. Rev., 1985, 85, 129.
171. de Grauw, C. F., Peters, J. A., van Bekkum, H., and Huskens, J., Synthesis, 1994, 1007.
172. For example: Kleiderer, E. C., and Kornfeld, E. C., J. Org. Chem., 1948, 13, 455.
173. Kellogg, R. M., in 'Comprehensive Organic Synthesis' (Ser. Eds B. M. Trost and I. Fleming) Vol. 8 (Ed. I. Fleming) p. 79 (Pergamon: Oxford 1993).
174. Ruchardt, C., Gerst, M., and Ebenhoch, J., Angew. Chem., Int. Ed. Engl., 1997, 36, 1406.
175. Choi, C., and Stock, L. M., J. Org. Chem., 1984, 49, 2871.
176. Wilds, A. L., Org. React, 1944, 2, 178.
177. Jackman, L. M., and Mills, J. A., Nature (London), 1949, 164, 789.
178. Djerassi, C., Org. React., 1951, 6, 207.
179. For example: Birch, A. J., 'To See the Obvious'p. 197 (American Chemical Society: Washington, DC, 1995); Hudlicky, T., Chem. Rev., 1996, 96, 3; Pariser, R., CHEMTECH, 1998, 28(6), 48.
180. For example: Birch, A. J., 'To See the Obvious'p. 197 (American Chemical Society: Washington, DC, 1995); Hudlicky, T., Chem. Rev., 1996, 96, 3; Pariser, R., CHEMTECH, 1998, 28(6), 48.
181. For example: Birch, A. J., 'To See the Obvious'p. 197 (American Chemical Society: Washington, DC, 1995); Hudlicky, T., Chem. Rev., 1996, 96, 3; Pariser, R., CHEMTECH, 1998, 28(6), 48.