C-H activation dependent Pd-catalyzed carbonylative coupling of (hetero)aryl bromides and polyfluoroarenes

Chemical Communications

Volumn 51, Issue 10, 2015, Pages 1870-1873

  Lian, Zhong ^a   Friis, Stig D ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; BROMINE DERIVATIVE; CARBON; CARBON MONOXIDE; HYDROGEN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYFLUOROARENE DERIVATIVE; UNCLASSIFIED DRUG; BROMIDE; FLUOROBENZENE;

ARTICLE; CARBONYLATION; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS; TEMPERATURE; CHEMICAL STRUCTURE; CHEMISTRY;

BROMIDES; CARBON MONOXIDE; CATALYSIS; FLUOROBENZENES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84921524253     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc09303h     Document Type: Article

References (54)

1. (a) K. Muller, C. Faeh and F. Diederich, Science, 2007, 317, 1881-1886;
2. (b) S. Purser, P. R. Moore, S. Swallow and V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320-330;
3. (c) J. M. Desimone, Z. Guan and C. S. Elsbernd, Science, 1992, 257, 945-947;
4. (d) D. O'Hagan, Chem. Soc. Rev., 2008, 37, 308-319.
5. E. A. Ilardi, E. Vitaku and J. T. Njardarson, J. Med. Chem., 2014, 57, 2832-2842.
6. C. Isanbor and D. O'Hagan, J. Fluorine Chem., 2006, 127, 303-319.
7. (a) N. A. Bumagin, I. G. Bumagina, A. N. Kashin and I. P. Beletskaia, Dokl. Akad. Nauk SSSR, 1981, 261, 1141-1144;
8. (b) W. S. Ojo, K. Jacob, E. Despagnet-Ayoub, B. K. Munoz, S. Gonell, L. Vendier, V. H. Nguyen and M. Etienne, Inorg. Chem., 2012, 51, 2893-2901;
9. (c) M. Arisawa, T. Ichikawa and M. Yamaguchi, Org. Lett., 2012, 14, 5318-5321.
10. (a) M. M. Kremlev, W. Tyrra, D. Naumann and Y. L. Yagupolskii, J. Fluorine Chem., 2005, 126, 1327-1331;
11. (b) Y. Yang, N. J. Oldenhuis and S. L. Buchwald, Angew. Chem., Int. Ed., 2013, 52, 615-619;
12. (c) L. Melzig, C. R. Diene, C. J. Rohbogner and P. Knochel, Org. Lett., 2011, 13, 3174-3177.
13. (a) N. Kuhl, M. N. Hopkinson, J. Wencel-Delord and F. Glorius, Angew. Chem., 2012, 124, 10382-10401;
14. (b) J. Wencel-Delord, T. Drc¸ge, F. Liu and F. Glorius, Chem. Soc. Rev., 2011, 40, 4740-4761;
15. (c) D. A. Colby, R. G. Bergman and J. A. Ellman, Chem. Rev., 2010, 110, 624-655;
16. (d) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147-1169;
17. (e) L. Ackermann, Chem. Rev., 2011, 111, 1315-1345.
18. (a) M. Lafrance, C. N. Rowley, T. K. Woo and K. Fagnou, J. Am. Chem. Soc., 2006, 128, 8754-8756;
19. (b) H. Q. Do and O. Daugulis, J. Am. Chem. Soc., 2008, 130, 1128-1129;
20. (c) H. H. Zhang, J. Dong and Q. S. Hu, Eur. J. Org. Chem., 2014, 1327-1332;
21. (d) C. Y. He, F. L. Qing and X. G. Zhang, Tetrahedron Lett., 2014, 55, 2962-2964.
22. (a) T. Xu and H. Alper, J. Am. Chem. Soc., 2014, 136, 16970-16973;
23. (b) W. Mägerlein, A. F. Indolese and M. Beller, Angew. Chem., Int. Ed., 2001, 40, 2856-2859;
24. (c) S. D. Friis, T. L. Andersen and T. Skrydstrup, Org. Lett., 2013, 15, 1378-1381;
25. (d) Z. Lian, S. D. Friis and T. Skrydstrup, Angew. Chem., Int. Ed., 2014, 53, 9582-9586;
26. (e) H. Li, H. Neumann, M. Beller and X.-F. Wu, Angew. Chem., Int. Ed., 2014, 53, 3183-3186.
27. (a) A. Maleckis, J. W. Kampf and M. S. Sanford, J. Am. Chem. Soc., 2013, 135, 6618-6625;
28. (b) S. L. Zhang, L. Shi and Y. Q. Ding, J. Am. Chem. Soc., 2011, 133, 20218-20229.
29. M. A. Campo and R. C. Larock, Org. Lett., 2000, 2, 3675-3677.
30. (a) A. McNally, B. Haffemayer, B. S. L. Collins and M. J. Gaunt, Nature, 2014, 510, 129-133;
31. (b) E. J. Yoo, M. Wasa and J. Q. Yu, J. Am. Chem. Soc., 2010, 132, 17378-17380.
32. (a) K. Inamoto, J. Kadokawa and Y. Kondo, Org. Lett., 2013, 15, 3962-3965;
33. (b) Z. H. Guan, M. Chen and Z. H. Ren, J. Am. Chem. Soc., 2012, 134, 17490-17493.
34. A. Tlili, J. Schranck, J. Pospech, H. Neumann and M. Beller, Angew. Chem., Int. Ed., 2013, 52, 6293-6297.
35. (a) P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp and T. Skrydstrup, J. Am. Chem. Soc., 2011, 133, 6061-6071;
36. (b) S. D. Friis, R. H. Taaning, A. T. Lindhardt and T. Skrydstrup, J. Am. Chem. Soc., 2011, 133, 18114-18117;
37. (c) P. Nordeman, L. R. Odell and M. Larhed, J. Org. Chem., 2012, 77, 11393-11398.
38. (a) M. Iizuka and Y. Kondo, Chem. Commun., 2006, 1739-1741;
39. (b) S. Klaus, H. Neumann, A. Zapf, D. Strubing, S. Hubner, J. Almena, T. Riemeier, P. Gross, M. Sarich, W. R. Krahnert, K. Rossen and M. Beller, Angew. Chem., Int. Ed., 2006, 45, 154-158;
40. (c) H. Neumann, A. Brennfuehrer and M. Beller, Chem. - Eur. J., 2008, 14, 3645-3652;
41. (d) T. L. Andersen, W. Caneschi, A. Ayoub, A. T. Lindhardt, M. R. C. Couri and T. Skrydstrup, Adv. Synth. Catal., 2014, 356, 3074-3082;
42. (e) O. Lagerlund and M. Larhed, J. Comb. Chem., 2006, 8, 4-6.
43. (a) M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz and J. Fraanje, Organometallics, 1995, 14, 3081-3089;
44. (b) J. R. Martinelli, D. A. Watson, D. M. M. Freckmann, T. E. Barder and S. L. Buchwald, J. Org. Chem., 2008, 73, 7102-7107;
45. (c) S. D. Friis, T. Skrydstrup and S. L. Buchwald, Org. Lett., 2014, 16, 4296-4299.
46. (a) A. Suzuki, J. Organomet. Chem., 1999, 576, 147-168;
47. (b) D. S. Surry and S. L. Buchwald, Angew. Chem., Int. Ed., 2008, 47, 6338-6361.
48. E. Vitaku, D. T. Smith and J. T. Njardarson, J. Med. Chem., 2014, DOI: 10.1021/jm501100b.
49. (a) A. T. Lindhardt, R. Simonssen, R. H. Taaning, T. M. Gøgsig, G. N. Nilsson, G. Stenhagen, C. S. Elmore and T. Skrydstrup, J. Labelled Compd. Radiopharm., 2012, 55, 411-418;
50. (b) R. Voges, J. R. Heys and T. Moenius, Preparation of Compounds Labeled with Tritium and Carbon-14, John Wiley & Sons, Ltd, 2009.
51. R. M. Claramunt, C. Lopez, C. Perez-Medina, M. Perez-Torralba, J. Elguero, G. Escames and D. Acuna-Castroviejo, Bioorg. Med. Chem., 2009, 17, 6180-6187.
52. J. S. Quesnel and B. A. Arndtsen, J. Am. Chem. Soc., 2013, 135, 16841-16844.
53. D. Lapointe and K. Fagnou, Chem. Lett., 2010, 39, 1119-1126.
54. X. F. Wu, P. Anbarasan, H. Neumann and M. Beller, Angew. Chem., Int. Ed., 2010, 49, 7316-7319.