Regioselectivity in alkenyl(aryl)-heteroaryl Suzuki cross-coupling reactions of 2,4-dibromopyridine. A synthetic and mechanistic study

Tetrahedron

Volumn 62, Issue 48, 2006, Pages 11063-11072

  Sicre, Cristina ^a   Alonso Gómez, J Lorenzo ^a   Cid, M Magdalena ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

2,4 Dibromopyridine; Palladium catalysis; Regioselectivity; Suzuki reaction

Indexed keywords

2,4 DIBROMOPYRIDINE; BORONIC ACID DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 33750182030     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.040     Document Type: Article

References (57)

1. Eldred G.E., and Lasky M.R. Nature 361 (1993) 724
2. Sakai N., Decatur J., Nakanishi K., and Eldred G.E. J. Am. Chem. Soc. 118 (1996) 1559
3. Ren R.X.-F., Sakai N., and Nakanishi K. J. Am. Chem. Soc. 119 (1997) 3619
4. Sicre C., and Cid M.M. Org. Lett. 7 (2005) 5737-5739
5. Kitamura A., Tanaka J., Ohtani I.I., and Higa T. Tetrahedron 55 (1999) 2487-2492
6. Yamamoto Y., Tanaka T., Yagi M., and Inamoto M. Heterocycles 42 (1996) 189-194
7. Yamamoto Y., Azuma Y., and Mitoh H. Synthesis (1986) 564-565
8. Stanetty P., Röhrling J., Schnürch M., and Miholovilovic M. Tetrahedron 62 (2006) 2380-2387
9. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
10. Miyaura N. J. Organomet. Chem. 653 (2002) 54-57
11. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359-1469
12. Suzuki A. J. Organomet. Chem. 576 (1999) 147-168
13. Bellina F., Carpita A., and Rossi R. Synthesis (2004) 2419-2440
14. Miyaura N. In: De Meijere A., and Diederich F. (Eds). Metal-catalyzed Cross-coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim 41-124 Chapter 2
15. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
16. Suzuki A. Chem. Commun. (2005) 4759-4763
17. For review, see:. Schröter S., Stock C., and Bach T. Tetrahedron 61 (2005) 2245-2267 and references therein
18. Samuel, I. D. W.; Burn, P. L.; Lo, S.-C. European Patent WO 2004020448, 2004.
19. Denhart D.J., Purandare A.V., Catt J.D., King H.D., Gao A., Deskus J.A., Poss M.A., Stark A.D., Torrente J.R., Johnson G., and Mattson R.J. Bioorg. Med. Chem. Lett. 14 (2004) 4249-4252
20. 2,4-Dibromopyridine (1) was prepared following the method reported. See:. den Hertog H.J. Recl. Trav. Chim. Pays-Bas 64 (1945) 85-101 See also Ref. 2
21. Arylboronic acids 2 are commercially available.
22. For 4-bromo-2-phenylpyridine (4a), see:
23. Comins D.L., and Mantlo N.B. J. Org. Chem. 50 (1985) 4410-4411 For 2-bromo-4-phenylpyridine (5a), see:
24. Gros P., and Fort Y. J. Org. Chem. 68 (2003) 2028-2029
25. Case F.H., and Kasper T.J. J. Am. Chem. Soc. 78 (1956) 5842-5844 For 2,4-diphenylpyridine (6a), see:
26. Katritzky A.R., Chapman A.V., Cook M.J., and Millet G.H. J. Chem. Soc., Perkin Trans. 1 (1980) 2743-2754
27. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550-9561
28. Shen W. Tetrahedron Lett. 38 (1997) 5575-5578
29. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 37 (1998) 3387-3388
30. 2], see:. Jasim N.A., Perutz R.N., Whitwood A.C., Braun T., Izundu J., Neumann B., Rothfeld S., and Stammler H.-G. Organometallics 23 (2004) 6140-6149
31. 4. Sometimes more than 8 mol % was needed to take the reaction to completion because 'palladium black' precipitated. It has also been reported that TONs for 2-bromopyridine are lower than for 3- or 4-bromopyridine. See:. Feuerstein M., Doucet H., and Santelli M. Tetrahedron Lett. 42 (2001) 5659-5662
32. Several examples of a Suzuki coupling reaction between 2-bromopyridine and electron-withdrawing boronic acids have been reported in the literature but all required higher temperatures than 25 °C to proceed.
33. Tsuboyama, A.; Okada, S.; Takiguchi, T.; Miura, S.; Moriyama, T.; Kamatani, J.; Furogori, M. European Patent Appl. 2002.
34. Chem. Abstr. 137 (2002) 239825
35. Boronic acid 3e is commercially available; 3f was prepared as reported, see:. Harvey R.G., Pataki J., Cortez C., Di Raddo P., and Yang C. J. Org. Chem. 56 (1991) 1210-1217
36. 2, 527.2250; found, 529.2274 and 527.2277.{A figure is presented}
37. Monomeric compounds of palladium were obtained from more basic phosphines.
38. Mantovani A. J. Organomet. Chem. 255 (1983) 385-394
39. Isobe K., Nanjo K., Nakamura Y., and Kawaguchi S. Bull. Chem. Soc. Jpn. 59 (1986) 2141-2149
40. Chin C.C.H., Yeo J.S.L., Loh Z.H., Vittal J.J., Henderson W., and Hor T.S.A. J. Chem. Soc., Dalton Trans. (1998) 3777-3784
41. A similar dimer complex was recently reported as a precatalyst for the Suzuki reaction between 2-bromopyridine and phenyl boronic acid, but the reaction has to be performed at 80 °C, see:. Beeby A., Bettington S., Fairlamb I.J.S., Goeta A.E., Kapdi A.R., Niemelä E.H., and Thompson A.L. New J. Chem. 28 (2004) 600-605 In our case the dimer was not active since, in order to attain high regioselectivity, we had to run the reaction at 25 °C
42. This result contrasts with what was found in other dihalopyridines, in which the monosubstitution product presents a reduced reactivity.
43. Woods C.R., Benaglia M., Toyota S., Hardcastle K., and Siegel J.S. Angew. Chem., Int. Ed. 67 (2001) 238-241
44. Puglisi A., Benaglia M., and Roncan G. Eur. J. Org. Chem. (2003) 1552-1558
45. See Figure 1 in Supplementary data.
46. Perrin D., and Armarego W. Purification of Laboratory Chemicals (1998), Pergamon, Oxford
47. Duan X.-F., Li X.-H., Li F.-Y., and Huang C.-H. Synth. Commun. 34 (2004) 3227-3233
48. Iino Y., and Nitta M. Bull. Chem. Soc. Jpn. 61 (1988) 2235-2237
49. Chambron J.C., and Sauvage J.P. Tetrahedron 43 (1987) 895-904
50. Chen C., and Munoz B. Tetrahedron Lett. 39 (1998) 3401-3404
51. Blout E.R., and Eager V.W. J. Am. Chem. Soc. 67 (1945) 1315-1319
52. Baker R., and Castro J.L. J. Chem. Soc., Perkin Trans. 1 (1990) 47-65
53. SMART (Control) and SAINT (Integration) Software (1994), Bruker Analytical X-ray Systems, Madison, WI
54. Sheldrick G.M. SADABS. A Program for Absorption Corrections (1996), University of Göttingen, Germany
55. Sheldrick G.M. SHELXS97. A Program for the Solution of Crystal Structures from X-ray Data (1997), University of Göttingen, Germany
56. Spek A.L. PLATON. A Multipurpose Crystallographic Tool (2001), Utrecht University, Utrecht, The Netherlands
57. Crystallographic data (excluding structure factors) for complex 8 have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 603585. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).