Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates

Journal of Organometallic Chemistry

Volumn 693, Issue 19, 2008, Pages 3171-3178

  Belabassi, Yamina ^a   Alzghari, Saeed ^a   Montchamp, Jean Luc ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

Aryl halides; Cross coupling; Heterocycles; Palladium; Phosphorus

Indexed keywords

AROMATIC COMPOUNDS; SYNTHESIS (CHEMICAL);

ARYL HALIDES; CROSS COUPLINGS; CROSS-COUPLING; ELECTROPHILES; HETEROCYCLES; PALLADIUM CATALYZED CROSS COUPLINGS; PD(OAC)2; PHOSPHONATES; PHOSPHORUS; SUBSTRATE REACTIVITY;

PALLADIUM;

EID: 50449107901     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.07.020     Document Type: Article

References (70)

1. Hirao T., Masunaga T., Ohshiro Y., and Agawa T. Tetrahedron Lett. 21 (1980) 3595
2. Hirao T., Masunaga T., and Yamada N. Bull. Chem. Soc. Jpn. 55 (1982) 909
3. For example. Kabachnik M.M., Solntseva M.D., and Beletskaya I.P. Russ. Chem. Bull. 46 (1997) 1491
4. Beletskaya I.P., Neganova E.G., and Veits Y.A. Russ. J. Org. Chem. 40 (2004) 1782
5. Zhong P., Xiong Z.X., and Huang X. Synth. Commun. 30 (2000) 273
6. Ayyappan P., Evans O.R., Foxman B.M., Wheeler K.A., Warren T.H., and Lin W. Inorg. Chem. 40 (2001) 5954
7. Kalek M., and Stawinski J. Organometal 26 (2007) 5840
8. Chauhan S.S., Varshney A., Verma B., and Pennington M.W. Tetrahedron Lett. 48 (2007) 4051
9. Montoneri E., Viscardi G., Bottigliengo S., Gobetto R., Chierotti M.R., Buscaino R., and Quagliotto P. Chem. Mater. 19 (2007) 2671
10. Vasylyev M.V., Wachtel E.J., Popovitz-Biro R., and Neumann R. Chem. Eur. J. 12 (2006) 3507
11. Suri J.T., Steiner D.D., and Barbas III C.F. Org. Lett. 7 (2005) 3885
12. Vasylyev M.V., Astruc D., and Neumann R. Adv. Synth. Catal. 347 (2005) 39
13. Ngo H.L., Hu A., and Lin W. J. Mol. Catal. A 215 (2004) 177
14. Oishi S., Kang S.-U., Liu H., Zhang M., Yang D., Deschampsc J.R., and Burke Jr. T.R. Tetrahedron 60 (2004) 2971
15. Muthukumaran K., Loewe R.S., Ambroise A., Tamaru S.-I., Li Q., Mathur G., Bocian D.F., Misra V., and Lindsey J.S. J. Org. Chem. 69 (2004) 1444
16. Evans O.R., Manke D.R., and Lin W. Chem. Mater. 14 (2002) 3866
17. Guerrero G., Mutin P.H., Dahan F., and Vioux A. J. Organomet. Chem. 649 (2002) 113
18. Liu W.-Q., Olszowy C., Bischoff L., and Garbay C. Tetrahedron Lett. 43 (2002) 1417
19. Kant M., Bischoff S., Siefken R., Gründemann E., and Köckritz A. Eur. J. Org. Chem. (2001) 477
20. Machnitzkia P., Nickela T., Stelzer O., and Landgrafeb C. Eur. J. Inorg. Chem. (1998) 1029
21. Villemin D., Elbilali A., Simeon F., Jaffres P.-A., Maheut G., Mosaddak M., and Hakiki A. J. Chem. Res. (S) (2003) 436
22. Prim D., Campagne J.-M., Joseph D., and Andrioletti B. Tetrahedron 58 (2002) 2041
23. For examples of Ni and Cu couplings see:. Ogawa T., Usuki N., and Ono N. J. Chem. Soc. Perkin Trans. 1 (1998) 2953
24. Fischer J., Schurmann M., Mehring M., Zachwieja U., and Jurkschat K. Organometallics 25 (2006) 2886
25. Yao Q., and Levchik S. Tetrahedron Lett. 47 (2006) 277
26. Kong D., and Clearfield A. Cryst. Growth Des. 5 (2005) 1767
27. Märkl v.G., Gschwendner K., Rötzer I., and Kreitmeier P. Helv. Chim. Acta 87 (2004) 825
28. Balthazor T.M., and Grabiak R.C. J. Org. Chem. 45 (1980) 5425
29. Tavs P. Chem. Ber. 103 (1970) 2428
30. Engel R., and Cohen J.I. Synthesis of Carbon-Phosphorus Bonds. 2nd ed. (2003), CRC Press, Boca Raton, FL
31. Schwan A.L. Chem. Soc. Rev. 33 (2004) 218
32. Gelman D., Jiang L., and Buchwald S.L. Org. Lett. 5 (2003) 2315
33. Huang C., Tang X., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 71 (2006) 5020
34. Rao H., Jin Y., Fu H., Jiang Y., and Zhao Y. Chem. Eur. J. 12 (2006) 3636
35. Reviews. Montchamp J.-L. Special. Chem. Mag. 26 (2006) 44
36. Montchamp J.-L. J. Organomet. Chem. 690 (2005) 2388
37. Cross-Coupling. Montchamp J.-L., and Dumond Y.R. J. Am. Chem. Soc. 123 (2001) 510
38. Dumond Y.R., and Montchamp J.-L. J. Organomet. Chem. 653 (2002) 252
39. Bravo-Altamirano K., Huang Z., and Montchamp J.-L. Tetrahedron 61 (2005) 6315
40. Bravo-Altamirano K., and Montchamp J.-L. Tetrahedron Lett. 48 (2007) 5755
41. Bravo-Altamirano K., and Montchamp J.-L. Org. Lett. 8 (2006) 4169
42. Coudray L., Bravo-Altamirano K., and Montchamp J.-L. Org. Lett. 10 (2008) 1123
43. Hydrophosphinylation. Deprèle S., and Montchamp J.-L. J. Org. Chem. 66 (2001) 6745
44. Deprèle S., and Montchamp J.-L. J. Am. Chem. Soc. 124 (2002) 9386
45. Deprèle S., and Montchamp J.-L. Org. Lett. 6 (2004) 3805
46. Ribière P., Bravo-Altamirano K., Antczak M.I., Hawkins J.D., and Montchamp J.-L. J. Org. Chem. 70 (2005) 4064
47. Bravo-Altamirano K., Abrunhosa-Thomas I., and Montchamp J.-L. J. Org. Chem. 73 (2008) 2292
48. Fry J.A., Samanamu C.R., Montchamp J.-L., and Richards A.F. Eur. J. Inorg. Chem. 463 (2008) 463
49. Samanamu C.R., Olmstead M.M., Montchamp J.-L., and Richards A.F. Inorg. Chem. 47 (2008) 3879
50. Samanamu C.R., Zamora E.N., Montchamp J.-L., and Richards A.F. J. Solid State Chem. 181 (2008) 1462
51. Samanamu C.R., Zamora E.N., Lesikar L.A., Montchamp J.-L., and Richards A.F. Cryst. Eng. Commun. (2008) 10.1039/b809504n
52. Y. Belabassi, S. Gouault-Bironneau, J.-L. Montchamp, in: Encyclopedia of Reagents for Organic Synthesis (eEROS), update article, 2006. (http://www.mrw.interscience.wiley.com/eros/articles/rb161/abstract-fs.html).
53. Samanamu C.R., and Richards A.F. Polyhedron 26 (2007) 923
54. Diisopropyl phosphite was purchased from TCI America (catalog # P0629) and used as received.
55. Gooßen L.J., and Dezfuli M.K. Synlett (2005) 445
56. Gennady G.M., and Roy C.H. J. Org. Chem. 26 (1961) 1895
57. Bulot J.J., Aboujaoude E.E., Collignon N., and Savignac P. Phosphorus and Sulfur 21 (1984) 197
58. McKenna C.E., and Schmidhuser J. J. Chem. Soc. Chem. Commun. (1979) 739
59. a s of heterocycles: pyridine, 5.2; pyrimidine, 1.3; pyrazine, 0.65.
60. Conary G.S., Russel A.A., Paine R.T., Hall J.H., and Ryan R.R. Inorg. Chem. 27 (1988) 3242
61. Kiselev A.S., Gakh A.A., Kagramanov N.D., and Semenov V.V. Mendel. Commun. 4 (1991) 128
62. Redmore D. J. Org. Chem. 41 (1976) 2148
63. Haase M., Gunther W., Gorls H., and Anders E. Synthesis (1999) 2071
64. Haase M., Goerls H., and Anders E. Synthesis (1998) 195
65. Redmore D. Phosphorus Sulfur Relat. Elem. 5 (1979) 271
66. Cates L.A., Li V.-S., Yakshe C.C., Fadeyi M.O., Andree T.H., Karbon E.W., and Enna S.J. J. Med. Chem. 27 (1984) 654
67. Cates L.A., and Rashed M.S. Pharm. Res. 6 (1984) 271
68. Huang C., Tang X., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 71 (2006) 8328
69. Hall C.D., Beer P.D., Powell R.L., and Naan M.P. Phosphorus, Sulfur Silicon Relat. Elem. 105 (1995) 145
70. Bennett R.D., Burger A., and Volk W.A. J. Org. Chem. 23 (1958) 940