Ligand controlled orthogonal base-assisted direct C-H bond arylation in oxa(thia)zole-4-carboxylate series. New insights in nCMD mechanism

Tetrahedron

Volumn 69, Issue 22, 2013, Pages 4375-4380

  Théveau, Laure ^a   Querolle, Olivier ^b   Dupas, Georges ^a   Hoarau, Christophe ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

Direct C H arylation; Ligand effect; NBO; Palladium catalysis; Selectivity

Indexed keywords

BROMOBENZENE; CESIUM; CHLOROBENZENE; NITROGEN; OXA(THIA)ZOLE 4 CARBOXYLATE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; RUBIDIUM; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL PROCEDURES; CHEMICAL REACTION; DEPROTONATION; PHENYLATION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; SUBSTITUTION REACTION;

THIA;

EID: 84876678844     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.073     Document Type: Article

References (67)

1. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094 5115
2. T.W. Lyons, and M.S. Sandford Chem. Rev. 110 2010 1147 1196
3. C.S. Yeung, and V.M. Dong Chem. Rev. 111 2011 1215 1292
4. C. Liu, H. Zhang, W. Shi, and A. Lei Chem. Rev. 111 2011 1780 1824
5. K.M. Engle, T.-S. Mei, M. Wasa, and J.-Q. Yu Acc. Chem. Res. 45 2012 788 802
6. J. Yamaguchi, A.D. Yamaguchi, and K. Itami Angew. Chem., Int. Ed. 51 2012 8960 9009
7. N. Kuhl, M.N. Hopkinson, J. Wencel-Delord, and F. Glorius Angew. Chem., Int. Ed. 51 2012 2 21
8. P.B. Arockian, C. Bruneau, and P.H. Dixneuf Chem. Rev. 112 2012 5879 5918
9. S.R. Neufeldt, and M.S. Sanford Acc. Chem. Res. 45 2012 936 946
10. L.-C. Campeau, D.R. Stuart, and K. Fagnou Aldrichimica Acta 40 2007 35 41
11. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
12. F. Bellina, and R. Rossi Tetrahedron 65 2009 10269 10310
13. J. Roger, A.L. Gottumukkala, and H. Doucet ChemCatChem 2 2010 20 40
14. L. Ackermann Chem. Commun. 46 2010 4866 4877
15. C. Fischmeister, and H. Doucet Green Chem. 13 2011 741 753
16. Y. Kondo, T. Komine, and T. Sakamoto Org. Lett. 2 2000 3111 3113
17. L.-C. Campeau, D. Schipper, and K. Fagnou J. Am. Chem. Soc. 130 2008 3266 3267
18. L.-C. Campeau, D. Schipper, and K. Fagnou J. Am. Chem. Soc. 130 2008 3276 3277
19. S. Yanagisawa, K. Ueda, H. Sekizawa, and K. Itami J. Am. Chem. Soc. 131 2009 14622 14623
20. N.A. Strotman, H.R. Chobanian, Y. Guo, J. He, and J.E. Wilson Org. Lett. 12 2010 3578 3581
21. M. Wasa, B.T. Worell, and J.-Q. Yu Angew. Chem., Int. Ed. 49 2010 1275 1277
22. D. Lapointe, T. Markiewicz, C.J. Whipp, A. Toderian, and K. Fagnou J. Org. Chem. 76 2011 749 759
23. P. Guo, J. Min Joo, S. Rakshit, and D. Sames J. Am. Chem. Soc. 133 2011 16338 16341
24. K. Si Larbi, H.Y. Fu, N. Laidaoui, K. Beydoun, A. Miloudi, D. El Abed, S. Djabbar, and H. Doucet ChemCatChem 4 2012 815 823
25. M. Catellani, and P. Chiusoli J. Organomet. Chem. 425 1992 151 154
26. S. Pivsa-Art, T. Datoh, Y. Kawamura, M. Miura, and M. Nomura Bull. Chem. Soc. Jpn. 71 1998 467 473
27. B. Glover, K.A. Harvey, B. Liu, M.J. Sharp, and M.F. Tymoschenko Org. Lett. 5 2003 301 304
28. C. Hoarau, A. Du Fou de Kerdaniel, N. Bracq, P. Grandclaudon, A. Couture, and F. Marsais Tetrahedron Lett. 46 2005 8573 8577
29. H.A. Chiong, and O. Daugulis Org. Lett. 9 2007 1449 1451
30. C. Gozzi, L. Lavenot, K. Ilg, V. Panalva, and M. Lemaire Tetrahedron Lett. 38 1997 8867 8870
31. L. Lavenot, C. Gozzi, K. Ilg, V. Penalva, and M. Lemaire J. Organomet. Chem. 567 1998 49 55
32. S.-Y. Tang, Q.-X. Guo, and Y. Fu Chem. - Eur. J. 17 2011 13866 13876
33. M. Steinmetz, K. Ueda, S. Grimme, J. Yamaguchi, S. Kirchberg, K. Itami, and A. Studer Chem. - Asian. J. 7 2012 1256 1260
34. J.J. González, N. García, B. Gómez-Lor, and A.M. Echavarren J. Org. Chem. 62 1997 1286 1291
35. D. García-Cuadrado, A.A.C. Braga, F. Maseras, and A.M. Echavarren J. Am. Chem. Soc. 128 2006 1066 1067
36. L.-C. Campeau, and K. Fagnou Chem. Commun. 2006 1253 1264
37. L.-C. Campeau, D.R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, and K. Fagnou J. Am. Chem. Soc. 131 2009 3291 3306
38. L. Ackermann Chem. Rev. 111 2011 1315 1345
39. S. Grosse, C. Pillard, S. Massip, J.-M. Léger, C. Jarry, B. Bourg, P. Bernard, and G. Guillaumet Chem. - Eur. J. 18 2012 14943 14947
40. H.A. Chiong, Q.-N. Pham, and O. Daugulis J. Am. Chem. Soc. 129 2007 9879 9884
41. B. Liégault, I. Petrov, S.I. Gorelsky, and K. Fagnou J. Org. Chem. 75 2010 1047 1060
42. H.-Y. Sun, S.I. Gorelsky, D.R. Stuart, L.-C. Campeau, and K. Fagnou J. Org. Chem. 75 2010 8180 8189
43. O. Rene, and K. Fagnou Adv. Synth. Catal. 352 2010 2116 2120
44. S. Gorelsky, D. Lapointe, and K. Fagnou J. Org. Chem. 77 2012 658 668
45. A. Petit, J. Flygare, A.T. Miller, G. Winkel, and D.H. Ess Org. Lett. 14 2012 3680 3683
46. M. Lafrance, and K. Fagnou J. Am. Chem. Soc. 128 2006 16496 16497
47. D. Balcells, E. Clot, and O. Eisenstein Chem. Rev. 110 2010 749 823
48. H.-Q. Do, R.M. Kashif Khan, and O. Daugulis J. Am. Chem. Soc. 130 2008 15185 15192
49. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074 1086
50. F. Bellina, S. Cauteruccio, and R. Rossi Curr. Org. Chem. 12 2008 774 790
51. R. Sanchez, and F.A. Zhuravlev J. Am. Chem. Soc. 129 2007 5824 5825
52. F.A. Zhuravlev Tetrahedron Lett. 47 2006 2929 2932
53. C. Verrier, T. Martin, C. Hoarau, and F. Marsais J. Org. Chem. 73 2008 7383 7386
54. T. Martin, C. Verrier, C. Hoarau, and F. Marsais Org. Lett. 10 2008 2909 2912
55. L. Théveau, C. Verrier, P. Lassalas, T. Martin, G. Dupas, O. Querolle, L. Van Hijfte, F. Marsais, and C. Hoarau Chem. - Eur. J. 17 2011 14450 14463
56. E. Vedejs, and S.D. Monahan J. Org. Chem. 61 1996 5192 5193
57. C.E. Kefalidis, O. Baudoin, and E. Clot Dalton Trans. 39 2010 10528 10535
58. Iodide poisoning effect of catalyst is known to inhibit CMD reactivity: L.-C. Campeau, M. Parisien, A. Jean, and K. Fagnou J. Am. Chem. Soc. 128 2006 581 590
59. S. Rousseaux, M. Davi, J. Sofack-Kreutzer, C. Pierre, C.E. Kefalidis, E. Clot, K. Fagnou, and O. Baudoin J. Am. Chem. Soc. 132 2010 10706 10716
60. B. Biswas, M. Sugimoto, and S. Sakaki Organometallics 19 2000 3895 3908
61. D.L. Davies, S.M.A. Donald, and S.A. Macgregor J. Am. Chem. Soc. 127 2005 13754 13755 Noteworthy, Clot et al. have recently reported the first computational study about energetics of bromide substitution with different bases, see Ref. 15
62. J.F. Flemming, M.C. Pilon, O.Y. Borbulevitch, M.Y. Antipin, and V.V. Grushin Inorg. Chim. Acta 280 1998 87 98
63. S. Kozuch, S. Shaik, A. Jutand, and C. Amatore Chem. - Eur. J. 10 2004 3072 3080
64. M. Kalek, and J. Stawinski Organometallics 26 2007 5840 5847
65. M. Kalek, and J. Stawinski Organometallics 27 2008 5876 5888
66. N2-type pathway on tricoordinated palladium(II) center, see Ref. 15. It has been previously demonstrated that monoligated palladium complex is the effective specie for the oxidative addition step affording a tricoordinated palladium(II) complex. See U. Christmann, and R. Vilar Angew. Chem., Int. Ed. 44 2005 366 374 and
67. G.C. Fu Acc. Chem. Res. 41 2008 1555 1564