Directed Functionalization of Halophenyl-2-oxazolines with TMPMgCl·LiCl

European Journal of Organic Chemistry

Volumn 2015, Issue 5, 2015, Pages 967-977

  Batista, João H C ^a   dos Santos, Fernanda M ^a   Bozzini, Leandro A ^a   Vessecchi, Ricardo ^a   Oliveira, Alfredo R M ^b   Clososki, Giuliano C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

Cross coupling; Density functional calculations; Heterocycles; Magnesium; Metalation; Regioselectivity

Indexed keywords

EID: 85027957629     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201403255     Document Type: Article

References (99)

1. For representative reviews, see:.
2. Frump, J.A., Chem. Rev. 71 (1971), 483–505.
3. Meyers, A.I., Reuman, M., Tetrahedron 41 (1985), 837–860.
4. Meyers, A.I., Gant, T.G., Tetrahedron 50 (1994), 2297–2360.
5. Zhang, N., Pompe, T., Amin, I., Luxenhofer, R., Werner, C., Jordan, R., Macromol. Biosci. 12 (2012), 926–936.
6. Bolomolova, A., Filippov, S.K., Starovoytova, L.A., Borislav, K.P., Sedlacek, O., Hruby, M., Stepanek, P., J. Phys. Chem. B 118 (2014), 4940–4950.
7. Schulz, A., Jaksch, S., Schubel, R., Wegener, E., Di, Z., Han, Y., Meister, A., Kressler, J., Kabanov, A.V., Luxenhofer, R., ACS Nano 8 (2014), 2686–2696.
8. .
9. Jeong, S.Y., Nguyen, Q.P.B., Kim, H.J., Kim, T.H., Bull. Korean Chem. Soc. 32 (2011), 4133–4136.
10. Chen, L., Ding, X., Gong, L., Meggers, E., Dalton Trans. 42 (2013), 5623–5626.
11. .
12. Ghosh, A.K., Mathivanan, P., Cappiello, J., Tetrahedron: Asymmetry 9 (1998), 1–45.
13. Johnson, J.S., Evans, D.A., Acc. Chem. Res. 33 (2000), 325–335.
14. Helmchen, G., Pfaltz, A., Acc. Chem. Res. 33 (2000), 336–345.
15. Lee, G.-J., Kim, T., Kim, J.N., Lee, U., Tetrahedron: Asymmetry 13 (2002), 9–12.
16. Hargaden, G.C., Guiry, P.J., Chem. Rev. 109 (2009), 2505–2550.
17. Desimoni, G., Faita, G., Jørgensen, K.A., Chem. Rev. 106 (2006), 3561–3651.
18. Degnan, B.M., Hawkins, C.J., Lavin, M.F., McCaffrey, E.J., Parry, D.L., van den Brenk, A.L., Watterst, D.J., J. Med. Chem. 32 (1989), 1349–1354.
19. Mander, L., Liu, H.-W., 1, vol., Comprehensive Natural Products II: Chemistry and Biology, 2010, Oxford, UK.
20. .
21. Snieckus, V., Chem. Rev. 90 (1990), 879–933.
22. Yus, M., Foubelo, F., Knochel), P., Handbook of Functionalized Organometallics, 2005, Weinheim, Germany.
23. Mulvey, R.E., Mongin, F., Uchiyama, M., Kondo, Y., Angew. Chem. Int. Ed. 46 (2007), 3802–3824.
24. Whisler, M.C., MacNeil, S., Beak, P., Snieckus, V., Angew. Chem. Int. Ed. 43 (2004), 2206–2225.
25. Zenzola, M., Degennaro, L., Trinchera, P., Carroccia, L., Giovine, A., Romanazzi, G., Mastrorilli, P., Rizzi, R., Pisano, L., Luisi, R., Chem. Eur. J. 20 (2014), 12190–12200.
26. .
27. Gant, T.G., Meyers, A.I., Tetrahedron 50 (1994), 2297–2360.
28. Beak, P., Meyers, A.I., Acc. Chem. Res. 19 (1986), 356–363.
29. Hagen, S.E., Domaglia, J.M., J. Heterocycl. Chem. 27 (1990), 1609–1616.
30. Meyers, A.I., Avila, W.B., Tetrahedron Lett. 21 (1980), 3335–3358.
31. Meyers, A.I., Avilla, W.B., J. Org. Chem. 46 (1981), 3881–3886.
32. Reuman, M., Meyers, A.I., Tetrahedron 41 (1985), 837–860.
33. Mortier, J., Curr. Org. Chem. 15 (2011), 2413–2447.
34. Robert, N., Martin, T., Grisel, J., Lazaar, J., Hoarau, C., Marsais, F., Tetrahedron Lett. 50 (2009), 1768–1770.
35. Robert, N., Bonneau, A.-L., Hoarau, C., Marsais, F., Org. Lett. 8 (2006), 6071–6074.
36. Meyers, A.I., Willemsen, J., Tetrahedron 54 (1998), 10493–10511.
37. Meyers, A.I., Gabel, R.A., Heterocycles 11 (1978), 133–138.
38. Meyers, A.I., Michelich, E.D., J. Am. Chem. Soc. 97 (1975), 7383–7385.
39. .
40. Kondo, Y., Shilai, M., Uchiyama, M., Sakamoto, T., J. Am. Chem. Soc. 121 (1999), 3539–3540.
41. Uchiyama, M., Miyoshi, T., Kajihara, Y., Sakamoto, T., Otani, Y., Ohwada, T., Kondo, Y., J. Am. Chem. Soc. 124 (2002), 8514–8515.
42. Uchiyama, M., Naka, H., Matsumoto, Y., Ohwada, T., J. Am. Chem. Soc. 126 (2004), 10526–10527.
43. Naka, H., Uchiyama, M., Matsumoto, Y., Wheatley, A.E.Y., McPartlin, M., Morey, J.V., Kondo, Y., J. Am. Chem. Soc. 129 (2007), 1921–1930.
44. L'Helgoual'ch, J.M., Bentabed-Ababsa, G., Chevallier, F., Yonehara, M., Uchiyama, M., Derdour, A., Mongin, F., Chem. Commun. 42 (2008), 5375–5377.
45. Bellamy, E., Bayh, O., Hoarau, C., Trécourt, F., Quéguiner, G., Marsais, F., Chem. Commun. 46 (2010), 7043–7045.
46. Uchiyama, M., Kobayashi, Y., Furuyama, T., Nakamura, S., Kajihara, Y., Miyoshi, T., Sakamoto, T., Yoshinori, K., Morokuma, K., J. Am. Chem. Soc. 130 (2008), 472–480.
47. .
48. Clososki, G.C., Rohbogner, C.J., Knochel, P., Angew. Chem. Int. Ed. 46 (2007), 7681–7684.
49. Rohbogner, C.J., Clososki, G.C., Knochel, P., Angew. Chem. Int. Ed. 47 (2008), 1503–1507.
50. Dong, Z., Clososki, G.C., Wunderlich, S.H., Unsinn, A., Li, J.S., Knochel, P., Chem. Eur. J. 15 (2009), 457–468.
51. Noji, T., Fujiwara, H., Okano, K., Tokuyama, H., Org. Lett. 15 (2013), 1946–1949.
52. Klatt, T., Roman, D.S., León, T., Knochel, P., Org. Lett. 16 (2014), 1232–1235.
53. Duez, S., Steib, A.K., Knochel, P., Org. Lett. 14 (2012), 1951–1953.
54. Haas, D., Mosrin, M., Knochel, P., Org. Lett. 15 (2013), 6162–6165.
55. Unsinn, A., Wunderlich, S.H., Jana, A., Karaghiosof, K., Knochel, P., Chem. Eur. J. 19 (2013), 14687–14696.
56. Haag, B., Mosrin, M., Ila, H., Malakhov, V., Knochel, P., Angew. Chem. Int. Ed. 50 (2011), 9794–9824.
57. Klatt, T., Markiewicz, J.T., Samann, C., Knochel, P., J. Org. Chem. 79 (2014), 4253–4269.
58. Unsinn, A., Rohbogner, C.J., Knochel, P., Adv. Synth. Catal. 355 (2013), 1553–1560.
59. Krasovskiy, A., Krasovskaya, V., Knochel, P., Angew. Chem. Int. Ed. 45 (2006), 2958–2961.
60. Schwekendiek, K., Glorius, F., Synthesis 18 (2006), 2996–3002.
61. Harvey, R.G., Cortez, C., Tetrahedron 53 (1997), 7101–7118.
62. .
63. De Crisci, A.G., Chung, K.L., Solis-Ibarra, A.G., Waymouth, R.M., Organometallics 32 (2013), 2257–2266.
64. Yi, J., Lu, X., Sun, Y.-Y., Xião, B., Liu, L., Angew. Chem. Int. Ed. 52 (2013), 12409–12413.
65. Peng, G., Quin, X., Min, S., Synlett 24 (2013), 1255–1259.
66. Binder, J.T., Cordier, C.J., Fu, G.C., J. Am. Chem. Soc. 134 (2012), 17003–17006.
67. Xufing, L., Jian, S., Yanyan, X., Delain, L., Organometallics 30 (2011), 3284–3292.
68. Deliberto, L.A., Souza, C.R., Naal, Z., Clososki, G.C., Tetrahedron 70 (2014), 3249–3258.
69. .
70. Rathman, T.-L., Bailey, W.F., Org. Process Res. Dev. 13 (2009), 144–151.
71. Pansegrau, P.D., Rieker, W.F., Meyers, A.I., J. Am. Chem. Soc. 110 (1988), 7178–7184.
72. Meyers, A.I., Pansegrau, P.D., J. Chem. Soc., Chem. Commun., 1985, 690–691.
73. Meyers, A.I., Pansegrau, P.D., Tetrahedron Lett. 24 (1983), 4935–4938.
74. .
75. Ho, J., Coote, M.L., Franco-Pérez, M., Gómez-Balderas, R., J. Phys. Chem. A 114 (2010), 11992–12003.
76. Ho, J., Coote, M.L., Theor. Chem. Acc. 125 (2010), 3–21.
77. .
78. Hyla-Kryspin, I., Grimme, S., Büker, H.H., Nibbering, N.M.M., Cottet, F., Schlosser, M., Chem. Eur. J. 11 (2005), 1251–1256.
79. Schlosser, M., Marzi, E., Cottet, F., Heinz, B.H., Nibbering, N.M.M., Chem. Eur. J. 7 (2001), 3511–3516.
80. Schlosser, M., Mongin, F., Porwisiak, J., Dmowski, W., Büker, H.H., Nibbering, N.M.M., Chem. Eur. J. 4 (1998), 1281–1286.
81. Büker, H.H., Nibbering, N.M.M., Espinosa, D., Mongin, F., Schlosser, M., Tetrahedron Lett. 38 (1997), 8519–8522.
82. .
83. Snégaroff, K., Nguyen, T.T., Marquise, N., Halauko, Y.S., Harford, P.J., Roisnel, T., Matulis, V.E., Ivanshkevisch, O.A., Chevallier, F., Wheatley, A.E.H., Gros, P.C., Mongin, F., Chem. Eur. J. 17 (2011), 13284–13297.
84. Kadiyala, R.R., Tilly, D., Nagaradja, E., Roisnel, T., Matulis, V.E., Ivashkevich, O.A., Halauko, Y.S., Chevallier, F., Gros, P.C., Mongin, F., Chem. Eur. J. 19 (2013), 7944–7960.
85. Chevallier, F., Halauko, Y.S., Pecceu, C., Nassar, I.F., Dam, T.U., Roisnel, T., Matulis, V.E., Ivashkevich, O.A., Mongin, F., Org. Biomol. Chem. 9 (2011), 4671–4684.
86. Chevallier, F., Blin, T., Nagaradja, E., Lassagne, F., Roisnel, T., Halauko, Y.S., Matulis, V.E., Ivashkevich, O.A., Mongin, F., Org. Biomol. Chem. 10 (2012), 4878–4885.
87. Halauko, S.Y., Matulis, V.E., Ivashkevich, O.A., Grigoriev, Y.V., Gaponik, P.N., Tetrahedron 66 (2010), 3415–3420.
88. Frischmuth, A., Fernández, M., Barl, N.M., Achrainer, F., Zipse, H., Berionni, G., Mayr, H., Karaghiosoff, K., Knochel, P., Angew. Chem. Int. Ed. 53 (2014), 7928–7932.
89. .
90. Becke, A.D., J. Chem. Phys. 98 (1993), 5648–5652.
91. Lee, C., Yang, W., Parr, R.G., Phys. Rev. B 37 (1988), 785–789.
92. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., Frisch, M.J., J. Phys. Chem. 98 (1994), 11623–11627.
93. .
94. García-Álvarez, P., Graham, D.V., Hevia, E., Kennedy, A.R., Klett, J., Mulvey, R.E., O'Hara, C.T., Weatherstone, S., Angew. Chem. Int. Ed. 47 (2008), 8079–8081.
95. Armstrong, D.R., García-Álvarez, P., Kennedy, A.R., Mulvey, R.E., Parkinson, J.A., Angew. Chem. Int. Ed. 49 (2010), 3185–3188.
96. Perrin, D.D., Amarego, W.L.F., Purification of Laboratory Chemicals, 1988, Oxford, UK.
97. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. W. M. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, revision C.02, Gaussian, Inc., Wallingford CT, 2004.
98. Stevens, W.J., Krauss, M., Basch, H., Jasien, P.G., Can. J. Chem. 70 (1992), 612–630.
99. Tomasi, J., Persico, M., Chem. Rev. 94 (1994), 2027–2094.