Copper-Free Sonogashira coupling in water with an amphiphilic resin-supported palladium complex

Tetrahedron

Volumn 66, Issue 5, 2010, Pages 1064-1069

  Suzuka, Toshimasa ^a   Okada, Yukari ^a   Ooshiro, Kazumasa ^a   Uozumi, Yasuhiro ^b  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMPHOPHILE; COPPER; HALIDE; MACROGOL; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYSTYRENE; RESIN; WATER;

ARTICLE; CATALYSIS; CATALYST; FILTRATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION;

EID: 73149083510     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.011     Document Type: Article

References (79)

1. Sonogashira K., and Tohda Y. Tetrahedron Lett. (1975) 4467
2. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
3. For reviews, see:
4. Chinchilla R., and Nájera C. Chem. Rev. 107 (2007) 874
5. Sonogashira K. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Reactions (1998), Wiley-VCH, New York, NY
6. Glaser C. Ber. Dtsch. Chem. Ges. 2 (1869) 422
7. Siemsen P., Livingston R.C., and Diederich F. Angew. Chem., Int. Ed. 39 (2000) 2632
8. For reviews on heterogeneous-switching, see:
9. Bailey D.C., and Langer S.H. Chem. Rev. 81 (1981) 109
10. Shuttleworth S.J., Allin S.M., and Sharma P.K. Synthesis (1997) 1217
11. Shuttleworth S.J., Allin S.M., Wilson R.D., and Nasturica D. Synthesis (2000) 1035
12. Dörwald F.Z. Organic Synthesis on Solid Phase (2000), Wiley-VCH, Weinheim
13. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217
14. McNamara C.A., Dixon M.J., and Bradley M. Chem. Rev. 102 (2002) 3275
15. In: De Vos D.E., Vankelecom I.F.J., and Jacobs P.A. (Eds). Chiral Catalyst Immobilization and Recycling (2000), WILEY-VCH, Weinheim
16. Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., and Taylor S.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3815
17. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
18. Uozumi Y. Top. Curr. Chem. 242 (2004) 77
19. Guino M., and Hii K.K.M. Chem. Soc. Rev. 36 (2007) 608
20. For recent studies on the copper-free Sonogashira coupling under heterogeneous conditions, see:
21. Lu N., Chen Y.-C., Chen T.-L., and Wu S.-J. J. Organomet. Chem. 694 (2009) 278 (fluorous biphasic system)
22. Komáromi A., and Novák Z. Chem. Commun. (2008) 4968 (palladium on charcoal)
23. Komura K., Nakamura H., and Sugi Y. J. Mol. Cat. A 293 (2008) 72 (palladium supported on MCM-41)
24. De Lima P.G., and Antunes O.A.C. Tetrahedron Lett. 49 (2008) 2506
25. Kim J.-H., Lee D.-H., Jun B.-H., and Lee Y.-S. Tetrahedron Lett. 48 (2007) 7079 (polymer-support)
26. Cwik A., Hell Z., and Figueras F. Tetrahedron Lett. 47 (2006) 3023
27. Tyrrell E., Al-Saardi A., and Millet J. Synlett (2005) 487
28. Djakovitch L., and Rollet P. Adv. Synth. Catal. 346 (2004) 1782 (zeolite)
29. Djakovitch L., and Rollet P. Tetrahedron Lett. 45 (2004) 1367 (zeolite)
30. Fukuyama T., Shinmen M., Nishitani S., Sato M., and Ryu I. Org. Lett. 4 (2002) 1691 (ionic liquid)
31. Bakherad M., Keivanloo A., Bahramian B., and Mihanparast S. Tetrahedron Lett. 50 (2009) 6418
32. For reviews on aqueous-switching, see:
33. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), Wiley-VCH, New York, NY
34. Grieco P.A. Organic Synthesis in Water (1997), Kluwer Academic, Dordrecht
35. Herrmann W.A., and Kohlpaintner C.W. Angew. Chem., Int. Ed. Engl. 32 (1993) 1524
36. Lindström U.M. Chem. Rev. 102 (2002) 2751
37. Li C.-J., and Chan T.-H. Comprehensive Organic Reactions in Aqueous Media (2007), Wiley-Interscience, New Jersey
38. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-Phase Organometallic Catalysis (2004), WILEY-VCH, Weinheim
39. For recent studies on the copper-free Sonogashira coupling under aqueous conditions, see:
40. Bakherad M., Keivanloo A., Bahramian B., and Hashemi M. Tetrahedron Lett. 50 (2009) 1557
41. Gu S., and Chen W. Organometallics 28 (2009) 909
42. Chandra A., Singh B., Upadhyay S., and Singh R.M. Tetrahedron 64 (2008) 11680
43. Komáromi A., Tolnai G.L., and Novák Z. Tetrahadron 49 (2008) 7294
44. Ines B., SanMartin R., Churruca F., Domingues E., Urtiaga M., Miren K., and Arriortua M.I. Organometallics 27 (2008) 2833
45. Shi S., and Zhang Y. Synlett (2007) 1843
46. Kawanami H., Matsushima K., Sato M., and Ikushima Y. Angew. Chem., Int. Ed. 46 (2007) 5129
47. Lipshutz B.H., Chung D.W., and Rich B. Org. Lett. 10 (2008) 3793
48. For copper-free Sonogashira coupling in water with immobilized catalysts, see:
49. Ye Z.-W., and Yi W.-B. J. Fluor. Chem. 129 (2008) 11124
50. Cai M., Xu Q., and Sha J. J. Mol. Cat. A 272 (2007) 293 Also see reference 11
51. Bayer E., and Rapp W. In: Voelter W., Bayer E., Ovchinikov Y.A., and Iwanov V.T. (Eds). Chemistry of Peptides and Proteins Vol. 3 (1986), Walter de Gruter, Berlin 3
52. Rapp W. In: Jung G. (Ed). Combinatorial Peptide and Nonpeptide Libraries (1996), VCH, Weinheim 425
53. Du X., and Armstrong R.W. J. Org. Chem. 62 (1997) 5678
54. Gooding O.W., Baudert D., Deegan T.L., Heisler K., Labadie J.W., Newcomb W.S., Porco Jr. J.A., and Eikeren P.J. J. Comb. Chem. 1 (1999) 113
55. For studies on polymer-supported transition metal complex catalysts from the author's group, see:
56. Uozumi Y., Danjo H., and Hayashi T. Tetrahedron Lett. 38 (1997) 3557 (allylic substitution)
57. Danjo H., Tanaka D., Hayashi T., and Uozumi Y. Tetrahedron 55 (1999) 14341 (allylic substitution)
58. Uozumi Y., Danjo H., and Hayashi T. J. Org. Chem. 64 (1999) 3384 (cross-coupling)
59. Uozumi Y., and Watanabe T. J. Org. Chem. 64 (1999) 6921 (carbonylation reaction)
60. Uozumi Y., and Nakai Y. Org. Lett. 4 (2002) 2997 (Suzuki-Miyaura coupling)
61. Uozumi Y., and Kimura T. Synlett (2002) 2045 (Heck reaction)
62. Uozumi Y., and Shibatomi K. J. Am. Chem. Soc. 123 (2001) 2919 (asymmetric alkylation)
63. Uozumi Y., Tanaka H., and Shibatomi K. Org. Lett. 6 (2004) 281 (asymmetric amination)
64. Hocke H., and Uozumi Y. Synlett (2002) 2049 (asymmetric catalysis)
65. Uozumi Y., and Nakazono M. Adv. Synth. Catal. 344 (2002) 274 (Rh catalysis)
66. Hocke H., and Uozumi Y. Tetrahedron 59 (2003) 619 (asymmetric catalysis)
67. Hocke H., and Uozumi Y. Tetrahedron 60 (2004) 9297 (asymmetric catalysis)
68. Nakai Y., and Uozumi Y. Org. Lett. 7 (2005) 291 (asymmetric cycloisomerization)
69. Uozumi Y., and Kikuchi M. Synlett (2005) 1775 (cross-coupling)
70. Uozumi Y., and Kimura M. Tetrahedron: Asymmetry 17 (2006) 161 (asymmetric etherification)
71. Kobayashi Y., Tanaka D., Danjo H., and Uozumi Y. Adv. Synth. Catal. 348 (2006) 1561 (asymmetric alkylation)
72. Uozumi Y., Suzuka T., Kawade R., and Takenaka H. Synlett (2006) 2109 (allylic azidation)
73. Uozumi Y., and Suzuka T. J. Org. Chem. 71 (2006) 8644 (nitromethylation)
74. Uozumi Y., and Suzuka T. Synthesis (2008) 1960 (allylic sulfonylation)
75. Uozumi Y., Takenaka H., and Suzuka T. Synlett (2008) 1557 (asymmetric desymmetrization)
76. Oe Y., and Uozumi Y. Adv. Synth. Catal. 350 (2008) 1771 (Kharasch reaction)
77. Uozumi Y., Matsuura Y., Arakawa T., and Yamada Y.M.A. Angew. Chem., Int. Ed. 48 (2009) 2708 (asymmetric Suzuki coupling)
78. PS-PEG beads are known to display relatively uniform swelling in a variety of solvents from medium to high polarity ranging from toluene to water to provide a solvent-swollen gel network, which allows relatively rapid diffusional access of reagents to reactive sites (see, Ref. 9 and references cited therein).
79. Preliminary results on aqueous, heterogeneous, copper-free Sonogashira coupling have been reported, see:. Uozumi Y., and Kobayashi Y. Heterocycles 59 (2003) 71