Improved Hiyama cross-coupling reactions using HOMSi®

Tetrahedron Letters

Volumn 52, Issue 52, 2011, Pages 7178-7181

  Marcuccio, Sebastian M ^a,b   Epa, Ruwan ^a   Moslmani, Maisa ^b   Hughes, Andrew B ^b  

^a LA TROBE UNIVERSITY   (Australia)

^b Unit 1   (Australia)

Author keywords

Cross coupling; Hiyama reaction; HOMSi ; Palladacycle; Tri o tolylphosphine

Indexed keywords

BROMOBENZOIC ACID DERIVATIVE; LIGAND; ORGANIC SOLVENT; PALLADIUM; PHOSPHINE DERIVATIVE; WATER;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION;

EID: 82255178998     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.126     Document Type: Article

References (67)

1. HOMSi® is a registered trademark of Advanced Molecular Technologies Pty Ltd, http://www.amtechpl.com/.
2. A. Suzuki Mod. Arene Chem. 2002 53 106
3. Zapf, A. Transition Metals for Organic Synthesis, 2nd ed., 2004, Vol. 1, pp 211-229.
4. J.-P. Corbet, and G. Mignani Chem. Rev. 106 2006 2651 2710
5. R. Narayanan Molecules 15 2010 2124 2138
6. Anon Heterocycles 80 2010 45 62
7. J.P. Wolfe, and J.S. Nakhla Name React. Homologations 2009 163 184
8. F. Alonso, I.P. Beletskaya, and M. Yus Tetrahedron 64 2008 3047 3101
9. Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed., 2002, Vol. 1, pp 591-598.
10. C. Chult, R.J.P. Corriu, C. Reye, and J.C. Young Chem. Rev. 93 1993 1371 1448
11. R. von Müller, M. Dressler, and C. Dathe J. Prakt. Chem. 312 1970 150 160
12. Selected references are given here: R. Müller, S. Reichel, and C. Dathe J. Prakt. Chem. 311 1969 930 935
13. R. Müller, and R. Koehne Z. Chem. 9 1969 429
14. R. Müller, R. Koehne, H.J. Model, and C. Dathe Z. Anorg. Allg. Chem. 368 1969 243 247
15. R. Müller, S. Reichel, and C. Dathe Inorg. Nucl. Chem. Lett. 3 1967 125 133
16. R. Müller, and C. Dathe Z. Anorg. Allg. Chem. 343 1966 150 153
17. R. Müller, C. Dathe, and H.J. Frey Chem. Ber. 99 1966 1614 1617
18. R. Müller, and C. Dathe Z. Anorg. Allg. Chem. 341 1965 49 60
19. R. Müller, and C. Dathe Z. Anorg. Allg. Chem. 341 1965 41 48
20. R. Müller, and W. Müller Chem. Ber. 98 1965 2916 2919
21. R. Müller Z. Chem. 5 1965 220 225
22. R. Müller, C. Dathe, and D. Mross Chem. Ber. 98 1965 241 244
23. R. Müller, and C. Dathe Chem. Ber. 98 1965 235 240
24. R. Müller, and E.G. Rochow J. Chem. Ed. 42 1965 41 47
25. R. Müller, and C. Dathe J. Prakt. Chem. 22 1963 232 240
26. J.-i. Yoshida, K. Tamao, H. Yamamoto, T. Kakui, T. Uchida, and M. Kumada Organometallics 1 1982 542 549
27. J.-i. Yoshida, K. Tamao, M. Takahashi, and M. Kumada Tetrahedron Lett. 1978 2161 2164
28. K. Tamao, T. Kakui, and M. Kumada Tetrahedron Lett. 1979 619 622
29. K. Tamao, H. Matsumoto, T. Kakui, and M. Kumada Tetrahedron Lett. 1979 1137 1140
30. J.-i. Yoshida, K. Tamao, T. Kakui, and M. Kumada Tetrahedron Lett. 1979 1141 1144
31. K. Tamao, J.-i. Yoshida, M. Takahashi, H. Yamamoto, T. Kakui, H. Matsumoto, A. Kurita, and M. Kumada J. Am. Chem. Soc. 100 1978 290 292
32. K. Tamao, T. Kakui, and M. Kumada J. Am. Chem. Soc. 100 1978 2269
33. J.-i. Yoshida, K. Tamao, A. Kurita, and M. Kumada Tetrahedron Lett. 1978 1809 1812
34. K. Ikenaga, K. Kikukawa, and T. Matsuda J. Chem. Soc., Perkin Trans. 1 1986 1959 1964
35. A. Hallberg, and C. Westerlund Chem. Lett. 1982 1993 1994
36. W.P. Weber, R.A. Felix, A.K. Willard, and K.E. Koenig Tetrahedron Lett. 1971 4701 4704
37. Y. Hatanaka, and T. Hiyama J. Org. Chem. 53 1988 920 923
38. S. Napier, S.M. Marcuccio, H. Tye, and M. Whittaker Tetrahedron Lett. 49 2008 6314 6315
39. H. Matsuhashi, M. Kuroboshi, Y. Hatanaka, and T. Hiyama Tetrahedron Lett. 35 1994 6507 6510
40. K. Shibata, K. Miyazawa, and Y. Goto Chem. Commun. 1997 1309 1310
41. Y. Hatanaka, and T. Hiyama J. Org. Chem. 54 1989 270 276
42. M.E. Mowery, and P. DeShong J. Org. Chem. 64 1999 1684 1688
43. S. Napier, S.M. Marcuccio, H. Tye, and M. Whittaker Tetrahedron Lett. 49 2008 3939 3942
44. P. Sehnal, R.J.K. Taylor, and I.J.S. Fairlamb Chem. Rev. 110 2010 824 889
45. H.M. Lee, and S.P. Nolan Org. Lett. 2 2000 2053 2055
46. S.E. Denmark, and Z. Wu Org. Lett. 1 1999 1495 1498
47. S.E. Denmark, and J.Y. Choi J. Am. Chem. Soc. 121 1999 5821 5822
48. K. Hirabayashi, J. Kawashima, Y. Nishihara, A. Mori, and T. Hiyama Org. Lett. 1 1999 299 301
49. S.E. Denmark, and D. Wehrli Org. Lett. 2 2000 565 568
50. S.E. Denmark, D. Wehrli, and J.Y. Choi Org. Lett. 2 2000 2491 2494
51. S.E. Denmark, and L. Neuville Org. Lett. 2 2000 3221 3224
52. H. Taguchi, K. Ghoroku, M. Tadaki, A. Tsubouchi, and T. Takeda J. Org. Chem. 67 2002 8450 8456
53. H. Taguchi, K. Takami, A. Tsubouchi, and T. Takeda Tetrahedron Lett. 45 2004 429 432
54. M. Shindo, K. Matsumoto, and K. Shishido Synlett 2005 176 179
55. 7th ed. J.E. Kogel, N.C. Trivedi, J.M. Barker, and S.T. Krukowski Industrial Minerals and Rocks 2006 Society for Mining, Metallurgy and Exploration
56. Y. Nakao, H. Imanaka, A.K. Sahoo, A. Yada, and T. Hiyama J. Am. Chem. Soc. 127 2005 6952 6953
57. Y. Nakao, A.K. Sahoo, H. Imanaka, A. Yada, and T. Hiyama Pure Appl. Chem. 78 2006 435 440
58. J. Chen, M. Tanaka, A.K. Sahoo, M. Takeda, A. Yada, Y. Nakao, and T. Hiyama Bull. Chem. Soc. Jpn. 83 2010 554 569
59. Y. Nakao, M. Takeda, T. Matsumoto, and T. Hiyama Angew. Chem. Int. Ed. 49 2010 4447 4450
60. A.K. Sahoo, T. Oda, Y. Nakao, and T. Hiyama Adv. Synth. Catal. 346 2004 1715 1727
61. Y. Nakao, A.K. Sahoo, A. Yada, J. Chen, and T. Hiyama Sci. Technol. Adv. Mater. 7 2006 536 543
62. Y. Nakao, H. Imanaka, J. Chen, A. Yada, and T. Hiyama J. Organomet. Chem. 692 2007 585 603
63. Y. Nakao, J. Chen, H. Imanaka, T. Hiyama, Y. Ichikawa, W.-L. Duan, R. Shintani, and T. Hayashi J. Am. Chem. Soc. 129 2007 9137 9143
64. Y. Nakao, J. Chen, M. Tanaka, and T. Hiyama J. Am. Chem. Soc. 129 2007 11694 11695
65. S. Tang, M. Takeda, Y. Nakao, and T. Hiyama Chem. Commun. 47 2011 307 309
66. S.J. Shirbin, B.A. Boughton, S.C. Zammit, S.D. Zanatta, S.M. Marcuccio, C.A. Hutton, and S.J. Williams Tetrahedron Lett. 51 2010 2979 2982
67. T. Hiyama Chem. Rev. 8 2008 337 350