Palladium-complex-catalyzed regioselective Markovnikov addition reaction and dehydrogenative double phosphinylation to terminal alkynes with diphenylphosphine oxide

Tetrahedron Letters

Volumn 48, Issue 27, 2007, Pages 4669-4673

  Dobashi, Naotomo ^a   Fuse, Kouichiro ^a   Hoshino, Takako ^a   Kanada, Jun ^a   Kashiwabara, Taigo ^a   Kobata, Chihiro ^a   Nune, Satish Kumar ^a   Tanaka, Masato ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Diphenylphosphine oxide; Homogeneous catalysis; Hydrophosphinylation; Palladium

Indexed keywords

1,2 DIPHENYLPHOSPHINYL 1 ALKENE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; DI(O TOLYL) PHENYLPHOSPHINE; DIPHENYLPHOSPHINE OXIDE; OXIDE; PALLADIUM 1,2 BIS(DIPHENYLPHOSPHINO)ETHANE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; PROPIONITRILE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; DEHYDROGENATION;

EID: 34249865379     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.039     Document Type: Article

References (82)

1. For a review, see:. Minami T., and Motoyoshiya J. Synthesis (1992) 333
2. For recent examples, see:. Ruder S.M., and Ding M. J. Chem. Soc., Perkin Trans. 1 (2000) 1771
3. Mizushima, E.; Han, L.-B.; Hayashi, T. Tanaka, M. Jpn. Patent 3,610,371, 2004.
4. Demchuk O.M., Pietrusiewicz K.M., Michrowska A., and Grela K. Org. Lett. 5 (2003) 3217
5. Kobayashi Y., and William A.D. Adv. Synth. Catal. 346 (2004) 1749
6. Leca D., Song K., Albert M., Gonçalves M.G., Fensterbank L., Lacôte E., and Malacria M. Synthesis (2005) 1405
7. Michrowska A., Bujok R., Harutyunyan S., Sashuk V., Dolgonos G., and Grela K. J. Am. Chem. Soc. 126 (2004) 9318
8. Rahman M.S., Oliana M., and Hii K.K. Tetrahedron: Asymmetry 15 (2004) 1835
9. Alajarin M., Lopez-Leonardo C., and Llamas-Lorente P. Lett. Org. Chem. 1 (2004) 145
10. Saratovskikh I.V., and Ragulin V.V. Russ. J. Gen. Chem. 75 (2005) 1077
11. Ono Y., and Han L.-B. Tetrahedron Lett. 47 (2006) 421
12. Welch F.J., and Paxton H.J. J. Polym. Sci., Part A: Gen. Pap. 3 (1965) 3427
13. Welch F.J., and Paxton H.J. J. Polym. Sci., Part A: Gen. Pap. 3 (1965) 3439
14. Shukla, J. R. U.S. Patent 4,241,145, 1980.
15. Levchik S.V., and Weil E.D. Polym. Int. 54 (2005) 11
16. Brunner H., and Pröbster M. Inorg. Chim. Acta 61 (1982) 129
17. Brown J.M., and Lucy A.R. J. Organomet. Chem. 314 (1986) 241
18. Krause H., and Döbler C. Catal. Lett. 8 (1991) 23
19. Okada Y., Minami T., Yamamoto T., and Ichikawa J. Chem. Lett. (1992) 547
20. Yamazaki A., Achiwa I., Horikawa K., Tsurubo M., and Achiwa K. Synlett (1997) 455
21. Rojas R., Valderrama M., and Garland M.T. J. Organomet. Chem. 689 (2004) 293
22. Ueno, S.; Shinohara, T.; Aramata, M.; Tanifuji, Y.; Inukai, T.; Ishizaka H. U.S. Patent 6,894,181, 2005.
23. For selected examples, see:. Chmutova M.K., Kochetkova N.E., and Myasoedov B.F. J. Inorg. Nucl. Chem. 42 (1980) 897
24. Rosen M., Nikolotova Z.I., and Kartasheva N.A. Radiokhim. 32 (1990) 70
25. Kabachnik M.I. Heteroatom Chem. 2 (1991) 1
26. For recent reviews, see:. Dembitsky V.M., Quntar A.A.A.A., Haj-Yehia A., and Srebnik M. Mini-Rev. Org. Chem. 2 (2005) 91
27. Tanaka M. Top. Curr. Chem. 232 (2004) 25
28. For selected recent examples, see:. Niu M., Fu H., Jiang Y., and Zhao Y. Chem. Commun. (2007) 272
29. Thielges S., Bisseret P., and Eustache J. Org. Lett. 7 (2005) 681
30. Han L.-B., and Zhao C.-Q. J. Org. Chem. 70 (2005) 10121
31. Montchamp J.-L. J. Organomet. Chem. 690 (2005) 2388
32. Ribiere P., Bravo-Altamirano K., Antczak M.I., Hawkins J.D., and Montchamp J.-L. J. Org. Chem. 70 (2005) 4064
33. Stone J.J., Stockland Jr. R.A., Reyes Jr. J.M., Kovach J., Goodman C.C., and Tillman E.S. J. Mol. Catal. A: Chem. 226 (2005) 11
34. Maffei M. Curr. Org. Synth. 1 (2004) 355
35. Tayama O., Nakano A., Iwahama T., Sakaguchi S., and Ishii Y. J. Org. Chem. 69 (2004) 5494
36. Deprèle S., and Montchamp J.-L. Org. Lett. 6 (2004) 3805
37. Kabalka G.W., and Guchhait S.K. Org. Lett. 5 (2003) 729
38. Gelman D., Jiang L., and Buchwald S.L. Org. Lett. 5 (2003) 2315
39. Gulykina N.S., Dolgina T.M., Bondarenko G.N., and Beletskaya I.P. Russ. J. Org. Chem. 39 (2003) 797
40. Takaki K., Koshoji G., Komeyama K., Takeda M., Shishido T., Kitani A., and Takehira K. J. Org. Chem. 68 (2003) 6554
41. Quntar A.A.A.A., Dembitsky V.M., and Srebnik M. Org. Lett. 5 (2003) 357
42. Peng A., and Ding Y. Synthesis (2003) 205
43. Takaki K., Komeyama K., and Takehira K. Tetrahedron 59 (2003) 10381
44. Bisaro F., and Gouverneur V. Tetrahedron Lett. 44 (2003) 7133
45. Lera M., and Hayes C.J. Org. Lett. 3 (2001) 2765
46. Beghetto V., Matteoli U., and Scrivanti A. Chem. Commun. (2000) 155
47. Han L.-B., and Tanaka M. J. Am. Chem. Soc. 118 (1996) 1571
48. Han L.-B., Choi N., and Tanaka M. Organometallics 15 (1996) 3259
49. Han L.-B., Hua R., and Tanaka M. Angew. Chem., Int. Ed. 37 (1998) 94
50. Zhao C.-Q., Han L.-B., Goto M., and Tanaka M. Angew. Chem., Int. Ed 40 (2001) 1929
51. Han, L.-B.; Zhao, C.-Q.; Tanaka, M. Int. Patent WO2002/064604.
52. Han, L.-B.; Zhang, C.; Tanaka, M. Int. Patent WO2003/097654.
53. Quite recently Oshima and co-workers reported an elegant radical reaction involving chlorodiphenylphosphine, diphenylphosphine, triethylamine, and a terminal alkyne leading to a 1,2-bis(diphenylphosphino)alkene, which could be readily oxidized with hydrogen peroxide to furnish a 1,2-bis(diphenylphosphinyl)alkene. See:. Sato A., Yorimitsu H., and Oshima K. Angew. Chem., Int. Ed. 44 (2005) 1694
54. It has been known that palladium acetate is reduced to generate Pd(0) species when treated with a phosphine; see:. Amatore C., Jutand A., and M'Barki M.A. Organometallics 11 (1992) 3009
55. Amatore C., Carré E., Jutand A., and M'Barki M.A. Organometallics 14 (1995) 1818
56. Double addition has been documented. See: (a) Ref. 6h.
57. Allen Jr. A., Manke D.R., and Lin W. Tetrahedron Lett. 41 (2000) 151
58. In view of possible oligomerization of 1a, we used a slight excess of 1a. For clearer understanding of the reaction profile forming both single and double phosphinylated products (3a, 4a, 5a, and 6a), however, the product yields in this particular reaction were tentatively calculated based on the quantity of 1a charged.
59. The higher branch-selectivity in this experiment (100 °C), as compared with the branch-selectivity (<5%) observed at 70 °C suggests that the higher reaction temperature is also a factor that enhances the branch-selectivity. See Ref. 7b.
60. Conversions of diphenylphosphine oxide in the reactions run in n-octane and ethanol were only 40% and 18%, respectively.
61. 3 and column chromatography using hexane/ethyl acetate (1/1) afforded 3a in 83% yield.
62. Despite the low yield of 4k, 5k, and 6k were not formed at all. We thank reviewers who recommended us to examine the reaction of trimethylsilylacetylene, which displayed the exceptional behavior.
63. Secondary phosphine oxides exist in two tautomeric isomers, P(O)H and P(OH), the former being dominant in the equilibrium. See:. Bailey W.J., and Fox R.B. J. Org. Chem. 28 (1963) 531
64. Bailey W.J., and Fox R.B. J. Org. Chem. 29 (1964) 1013
65. Hamilton L.A., and Landis P.S. In: Kosolapoff G.M., and Maier L. (Eds). Organic Phosphorus Compounds Vol. 4 (1972), Wiley, New York Chapter 11
66. Obtained from a mixture resulting from an uncatalyzed reaction of (p-tolylethynyl)diphenylphosphine oxide (8) with 2 run at 100 °C for 3 h in toluene (vide infra).
67. In the present reaction of p-tolylacetylene, we do have detected a trace of (p-tolylethynyl)diphenylphosphine oxide.
68. Prepared by hydrogen peroxide oxidation of (p-tolylethynyl)diphenylphosphine. See:. Liu B., Wang K.K., and Petersen J.L. J. Org. Chem. 61 (1996) 8503
69. Beletskaya I.P., Afanasiev V.V., Kazankova M.A., and Efimova I.V. Org. Lett. 5 (2003) 4309
70. Han L.-B., and Tanaka M. Shokubai 41 (1999) 577
71. For selected examples of apparent trans-insertion involving late transition metal complexes, see:. Green M., and Taylor S.H. J. Chem. Soc., Dalton Trans. (1975) 1142
72. Ojima I., Clos N., Donovan R.J., and Ingallina P. Organometallics 9 (1990) 3127
73. Yamashita H., Tanaka M., and Goto M. Organometallics 12 (1993) 988
74. Jun C.-H., and Crabtree R.H. J. Organomet. Chem. 447 (1993) 177
75. Mori A., Takahisa E., Kajiro H., Hirabayashi K., Nishihara Y., and Hiyama T. Chem. Lett. 27 (1998) 443
76. Faller J.W., and D'Alliessi D.G. Organometallics 21 (2002) 1743
77. For mechanistic aspects of apparent trans-insertion, see:. Nakamura A., and Otsuka S. J. Mol. Catal. 1 (1975/76) 285
78. Huggins J.M., and Bergman R.G. J. Am. Chem. Soc. 103 (1981) 3002
79. Clark H.C., Ferguson G., Goel A.B., Janzen E.G., Ruegger H., Siew P.Y., and Wong C.S. J . Am. Chem. Soc. 108 (1986) 6961
80. Selmeczy A.D., and Jones W.D. Inorg. Chim. Acta 300-302 (2000) 138
81. Crabtree R.H. New J. Chem. 27 (2003) 771
82. Trost B.M., and Ball Z.T. J. Am. Chem. Soc. 127 (2005) 17644