Efficient Catalytic Systems for Synthesis of 5,5''-Dibromo-2,2':6',2''-terpyridine and 5,5'-Dibromo-2,2'-bipyridine via Coupling of Dihalogenopyridines with 5-Bromo-2-trialkylstannylpyridines

• Autorzy: Krompiec S. , Ignasiak H. , Krompiec M. , Stanek Ł. , Filapek M. , Gębarowska K. , Penczek R.
• Języki publikacji: EN

Abstrakty

EN

The results of the studies on the synthesis of 5,5'-dibromo-2,2'-bipyridine and 5,5''-dibromo-2,2':6',2''-terpyridine via coupling of 5-bromo-2-iodopyridine and 2,6-dihalogenopyridines with 5-bromo-2-trialkylstannylpyridines mediated by palladium catalysts have been presented. The catalytic activity of the Pd(II) and Pd(0) complexes (e.g. [PdCl2(PPh3)2], [PdCl2(COD)], [Pd(dba)2]), and catalytic systems generated in situ from a stable precursor (e.g. [PdCl2], [Pd(acac)2]) and an external ligand (APh3, where A = P, As, Sb; phosphines, phosphites) in the coupling of diiodopyridine with 5-bromo-2-tributylstannylpyridine was investigated. The most active system was that generated from [Pd(acac)2] and P(OPh)3, while the highest coupling selectivity was achieved with [Pd(acac)2] and PPh3. The catalytic activity of systems containing chelating ligands BINAP or dppf was slightly inferior. In all reactions the formation of 5,5'-dibromo- 2,2'-bipyridine, the product of homocoupling of 5-bromo-2-tributylstannylpyridine, was observed. An increase of the L/Pd ratio for catalytic system generated from [Pd(acac)2] and P(OPh)3 resulted in improved selectivity of dbtpy formation (the yield of dbbpy, the product of homocoupling, decreased) and in an increased stability of the catalytic system (without decreasing the reaction rate even for Pd/L = 1:32). On the other hand, for the systems containing phosphines the increase of L/Pd above 4:1 for monodentate phosphines and above 2:1 forbidentate phosphines resulted in a fast decrease of the reaction rate. The coupling is faster for 2,6-diiodopyridine and slower for 2,6-dibromo pyridine, while 2,6-dichloropyridine is nonreactive. The yield of coupling for trimethyl- and tributylstannyl derivatives is practically identical. Particularly advantageous solvents for the studied coupling reaction are xylene, toluene, and 1,2-diethoxyethane.

Słowa kluczowe

EN

Stille coupling; palladium catalyst; dibromoterpyridine synthesis; dibromobipyridine synthesis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 2
• Strony: 245--262
• Opis fizyczny: Bibliogr. 53 poz., rys.

Twórcy

autor

Krompiec S.

autor

Ignasiak H.

autor

Krompiec M.

autor

Stanek Ł.

autor

Filapek M.

autor

Gębarowska K.

autor

Penczek R.

• Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia in Katowice, Szkolna 9, 40-007 Katowice, Poland,

Bibliografia

• 1.   Kaes C., Katz A. and Hosseini M.W., Chem. Rev., 100, 3553 (2000).
• 2.   Evans R.C., Douglas P. and Winscom C.J., Coord. Chem. Rev., 250, 2093 (2006).
• 3.   Cargill Thompson A.M.W., Coord. Chem. Rev., 160, l (1997).
• 4.   Fallahpour R.-A., Synthesis, 155 (2003).
• 5.   Heller M. and Schubert U.S., Eur. J. Org. Chem., 947 (2003).
• 6.   Zhu S.S. and Swager T.M., Adv. Mater., 8, 497 (1996).
• 7.   Zhu S.S. and Swager T.M., J. Am. Chem. Soc., 119, 12568 (1997).
• 8.   Zotti G., Zecchin S., Schiavon G. and Berlin A., J. Electroanal. Chem., 506, 106 (2001).
• 9.   Trouillet L., Lapkowski M., Stephan O. and Guillerez S., Synthetic Metals, 109, 277 (2000).
• lO. Hjelm J., Handel R.W., Hagfeldt A., Constable E.C., Housecroft C.E. and Foster R.J., Inorg. Chem., 44, 1073(2004).
• 11.  Goze C., Kozlov D.V., Castellano F.N., Suffert J. and Ziessel R., Tetrahedron Lett., 44, 8713 (2003).
• 12.  Constable E.C., Handel R.W., Housecroft C.E., Morales A.F., Flamigni L. and Barigelletti F., Dalton Trans., 1220(2003).
• 13.  Han F.-S., Higuchi M. and Kurth D.G., Tetrahedron, 64, 9108 (2008).
• 14.  Hormeier H. and Schubert U.S., Chem. Soc. Rev., 33, 373 (2004).
• 15.  Aoyama N., Hamada T, Manabe K. and Kobayashi S., Chem. Commun., 676 (2003).
• 16.  Ura Y., Tsujita H., Mitsudo T. and Kondo T, Bull. Korean Chem. Soc., 28, 2139 (2007).
• 17.  Collason B.X., Dietrich-Buchecker C. and Sauvage J.-P., Synlett., 271 (2002).
• 18.  Cardenas DJ. and Sauvage J.-P., Synlett., 916 (1996).
• 19.  Heller M. and Schubert U.S., Eur. J. Org. Chem., 947 (2003).
• 20.  For examples of Stille reactions: Galaup Ch., Couchet J.-M, Bedel S., Tisnes P. and Picard C., J. Org. Chem., 70,2274 (2005); Martineau D., Gros P. and Fort Y., J. Org. Chem., 69,7914 (2004); Champouret Y.D.M., Chaggar R.K., Dadhiwala L, Fawcert J. and Solan G.A., Tetrahedron, 62, 79 (2006); Gavina P. and Tatay S., Tetrahedron Lett., 47, 3471 (2006); Brotschi Ch., Mathis G. and Leumann Ch.J., Chem. Eur. J., 11, 1911 (2005); Mathieu J. and Marsura A., Synth. Commun., 33, 409 (2003); Shen X.,Moriuchi T. and Hirao T, Tetrahedron Lett., 44, 7711 (2003); Puglisi A., Bengalia M. and Roncan G.,' Eur. J. Org. Chem., 1552 (2003).
• 21. For examples of Negishi reactions: Lutzen A., Hapke M., Staats H. and Bunzen J., Eur. J. Org. Chem., 3948 (2003); Savage S.A., Smith A.P. and Fraser C.L., J. Org. Chem., 63, 10048 (1998); Mongin F., Trecourt F., Mongin O. and Quéguiner G., Tetrahedron, 58, 309 (2002); Hicks R.G., Koivisto B.D. and Lemaire M.T., Org. Lett., 6,1887 (2004); Nshimyumukiza R, Cahard D., Rouden J., Lasneb M.-C. and Plaqueventa J.-C., Tetrahedron Lett., 42, 7787 (2001).
• 22. Pierrat R, Gros R and Fort Y, Organie Lett., 7, 697 (2005).
• 23. Ishiyama T., Ishida K. and Miyaura N., Tetrahedron, 57, 9813 (2001).
• 24. Fuller A.A., Hester H.R., Salo E.V. and Stevens E.R, Tetrahedron Lett., 44, 2935 (2003).
• 25. Krompiec S., Krompiec M., Ignasiak H., Łapkowski M., Baj S. and Grabarczyk D., Catal. Comm., 8, 1457 (2007).
• 26. Krompiec S., Kuźnik N., Krompiec M., Penczek R., Mrzigod J. and Tórz A., J. Mol. Catal. A: Chem., 253,132(2006).
• 27. Kuźnik N. and Krompiec S., Coord. Chem. Rev., 251, 222 (2007).
• 28. Krompiec S., Krompiec M., Penczek R. and Ignasiak H., Coord Chem. Rev., 252, 1819 (2008).
• 29. Krompiec S., Penczek R., Kuźnik N., Małecki J.G. and Matlengiewicz M., Tetrahedron Lett., 48, 137 (2007).
• 30. Hegedus L.S., Organopalladium Chemistry, Chap. X in: M. Schlosser (ed.), Organometallics in Synthesis (A Manual), 2nd ed., Wiley, New York (2002).
• 31. Espinet R and Echavarren A.M., Angew. Chem. Int. Ed. Engl., 43, 4704 (2004).
• 32. Farina V. and Krishnan B., J. Am. Chem. Soc., 113, 9585 (1991).
• 33. Farina V., Krishnamurthy V. and Scott W.J., Org. React., Vol. 50, 1-704 (1997).
• 34. Ju J., Nam H., Jung H.M. and Lee S., Tetrahedron Lett., 47, 8673 (2006).
• 35. Amatore Ch. and Jutand A., J. Organomet. Chem., 576, 254 (1999).
• 36. Belykh L.B., Goremyka T.V., Gusarova N.K., Sukhov B.G. and Shmidt F.K., Kinet. Katal., 46, 572 (2006).
• 37. Oshima N., Maruyama Y, Okita K. and Imamura T., Jpn Patent 106,829 (2007); C.A., 146, 442622s (2007).
• 38. Tokuyasu J., Okuno T., Hori T. and Iwasaki H., PCT Int. Appl. WO 121,059 (2005); CA., 146, 53383a(2007).
• 39. Estrine B., Bouquillon S., Henin F. and Muzart J., Eur. J. Org. Chem., 2914 (2004).
• 40. Yang S.-C, Hsu Y-C. and Gan K.-H., Tetrahedron, 62, 3949 (2006).
• 41. Lehmann U. and Schluter A.D., Eur. J. Org. Chem., 3483 (2000).
• 42. Dupont J., Consorti C.S. and Spencer J., Chem Rev., 105, 2527 (2005).
• 43. Okeya S., Nakamura Y and Kawaguchi S., Bull. Chem. Soc. Jpn., 54, 3396 (1981).
• 44. Baba S., Ogura T. and Kawaguchi S., Bull. Chem. Soc. Jpn., 47, 665 (1974).
• 45. Okeya S., Sazaki H., Ogita M., Takemoto T, Onuki Y, Nakamura Y, Mohapatra B.K. and Kawaguchi S., Bull. Chem. Soc. Jpn., 54, 1978 (1981).
• 46. Trzeciak A.M., Ciunik Z. and Ziółkowski J.J., Organometallics, 21, 132 (2002).
• 47. Newkome G.R. and Roper J.M., J. Organomet. Chem., 186, 147 (1980).
• 48. Lehmann U., Henze O. and Schluter A.D., Chem. Eur. J., S, 854 (1999).
• 49. Case F.H., J. Am. Chem. Soc., 68, 2574 (1946).
• 50. Burstall F.H., J. Chem. Soc., 1662 (1938).
• 51. Romero F.M. and Ziessel R., Tetrahedron Lett., 36, 6471 (1995).
• 52. Bruce J.I., Chambron J.-C., Kolie P. and Sauvage J.-R, J. Chem. Soc. Perkin Trans, 1, 10,1226 (2002).
• 53. Bai X.-L., Liu X.-D., Wang M., Kang C.-Q. and Gao L.-X., Synthesis, 3, 458 (2005).