Palladium-catalyzed direct arylations of heteroarenes with tosylates and mesylates

Angewandte Chemie - International Edition

Volumn 48, Issue 1, 2009, Pages 201-204

  Ackermann, Lutz ^a   Althammer, Andreas ^a   Fenner, Sabine ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

C H activation; Direct arylation; Heteroarenes; Palladium; Sulfonates

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; PALLADIUM;

ARYLATIONS; C-H ACTIVATION; CHEMICAL EQUATIONS; DIRECT ARYLATION; ELECTROPHILES; H BONDS; HETEROARENES; PALLADIUM COMPLEXES; SULFONATES;

PALLADIUM COMPOUNDS;

EID: 58249118877     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804517     Document Type: Article

References (59)

1. a) M. Beller, C. Bolm, Transition Metals for Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim, 2004;
2. b) L. Ackermann, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009.
3. J. Tsuji, Palladium Reagents and Catalysts, 2nd ed., Wiley, New York, 2004.
4. Selected recent contributions from our laboratories: a) L. Ackermann, J. H. Spatz, C. J. Gschrei, R. Born, A. Althammer, Angew. Chem. 2006, 118, 7789-7792;
5. Angew. Chem. Int. Ed. 2006, 45, 7627-7630;
6. b) L. Ackermann, C. J. Gschrei, A. Althammer, M. Riederer, Chem. Commun. 2006, 1419-1421.
7. a) I. J. S. Fairlamb, Chem. Soc. Rev. 2007, 36, 1036-1045;
8. b) G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644-4680;
9. c) M. Schnürch, R. Flasik, A. F. Khan, M. Spina, M. D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem. 2006, 3283-3307;
10. d) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563;
11. Angew. Chem. Int. Ed. 2005, 44, 4442-4489;
12. e) S. Schroeter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245-2267, and references cited therein.
13. Recent reviews: a) B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949-957;
14. b) J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025;
15. c) T. Satoh, M. Miura, Top. Organomet. Chem. 2007, 24, 61-84;
16. d) L. Ackermann, Top. Organomet. Chem. 2007, 24, 35-60;
17. e) D. Kalyani, M. S. Sanford, Top. Organomet. Chem. 2007, 24, 85-116;
18. f) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238;
19. g) S. Pascual, P. de Mendoza, A. M. Echavarren, Org. Biomol. Chem. 2007, 5, 2727-2734;
20. h) L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35-41;
21. i) L. Ackermann, Synlett 2007, 507-526;
22. j) O. Daugulis, V. G. Zaitsev, D. Shabashov, Q. N. Pham, A. Lazareva, Synlett 2006, 3382-3388;
23. k) J.-Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041-4047.
24. a) I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173-1193;
25. b) a recent example: H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404-12405.
26. For examples of palladium-catalyzed coupling reactions with aryl tosylates, see: a) Suzuki-Miyaura couplings: C. M. So, C. Po Lau, F. Y. Kwong, Angew. Chem. 2008, 120, DOI: 10.1002/ange.200803193;
27. Angew. Chem. Int. Ed. 2008, 47, DOI: 10.1002/anie.200803193;
28. b) H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818-11819;
29. c) Negishi couplings: J. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 12527-12530;
30. d) Kumada-Corriu couplings: L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457-3460;
31. e) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704-8705;
32. f) Hiyama couplings: L. Zhang, J. Wu, J. Am. Chem. Soc. 2008, 130, DOI: 10.1021/ja804672m;
33. g) Mizoroki-Heck reactions: J.-P. Ebran, A. L. Hansen, T. M. Gogsig, T. Skrydstrup, J. Am. Chem. Soc. 2007, 129, 6931-6942;
34. h) Sonogashira reactions: D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175-6178;
35. Angew. Chem. Int. Ed. 2003, 42, 5993-5996;
36. i) carbonylations: R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754-2755, and references cited therein.
37. For ruthenium-catalyzed direct arylation of arenes using tosylates, see: L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681-2685;
38. Angew. Chem. Int. Ed. 2006, 45, 2619-2622.
39. B. M. Trost, Angew. Chem. 1995, 107, 285-307;
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
41. For selected recent examples, see: a) S. I. Kozhushkov, D. S. Yufit, L. Ackermann, Org. Lett. 2008, 10, 3409-3412;
42. b) L. Ackermann, A. Althammer, R. Born, Synlett 2007, 2833-2836;
43. c) L. Ackermann, R. Born, P. Álvarez-Bercedo, Angew. Chem. 2007, 119, 6482-6485;
44. Angew. Chem. Int. Ed. 2007, 46, 6364-6367;
45. d) L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652-1654;
46. Angew. Chem. Int. Ed. 2007, 46, 1627-1629;
47. e) L. Ackermann, Org. Lett. 2005, 7, 3123-3125.
48. R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, DOI: 10.1021/ar800036s.
49. A Recent example of the use of pivalic acid in palladium-catalyzed direct arylation: S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848-10849.
50. Selected recent reviews: a) H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 2007, 19, 2197-2208;
51. b) Y. L. Angell, K. Burgess, Chem. Soc. Rev. 2007, 36, 1674-1689;
52. c) D. Fournier, R. Hoogenboom, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1369-1380;
53. d) J.-F. Lutz, Angew. Chem. 2007, 119, 1036-1043;
54. Angew. Chem. Int. Ed. 2007, 46, 1018-1025.
55. For direct arylation of the 1,2,3-triazoles 5 with aryl chlorides, see: a) M. Iwasaki, H. Yorimitsu, K. Oshima, Chem. Asian J. 2007, 2, 1430-1435;
56. b) L. Ackermann, R. Vicente, R. Born, Adv. Synth. Catal. 2008, 350, 741-748;
57. c) for the use of aryl bromides as electrophiles, see: S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett. 2007, 9, 2333-2336.
58. For copper- or ruthenium-catalyzed direct arylation of substrates having 1,2,3-triazoles units, see: a) L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett. 2008, 10, 3081-3084;
59. b) L. Ackermann, R. Vicente, A. Althammer, Org. Lett. 2008, 10, 2299-2302.