Palladium on charcoal-catalyzed ligand-free Stille coupling

Tetrahedron

Volumn 66, Issue 45, 2010, Pages 8654-8660

  Yabe, Yuki ^a   Maegawa, Tomohiro ^a,b   Monguchi, Yasunari ^a   Sajiki, Hironao ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Atmospheric condition; Heterogeneous catalysis; Ligand free; Palladium; Stille coupling

Indexed keywords

ARSENIC; CHARCOAL; CHLORIDE; HALIDE; IODIDE; LITHIUM CHLORIDE; PALLADIUM; PHOSPHINE; TIN DERIVATIVE; TRIBUTYLTIN;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STILLE REACTION; SYNTHESIS;

EID: 77958070099     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.027     Document Type: Article

References (62)

1. M. Kosugi, K. Sasazawa, Y. Shimizu, and T. Mighita Chem. Lett. 1977 301 302
2. M. Kosugi, K. Sasazawa, Y. Shimizu, and T. Mighita Chem. Lett. 1977 1423 1424
3. D. Milstein, and J.K. Stille J. Am. Chem. Soc. 100 1978 3636 3638
4. D. Milstein, and J.K. Stille J. Am. Chem. Soc. 101 1979 4992 4998
5. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem., Int. Ed. 44 2005 4442 4489
6. J. Hassan, M. Sévignou, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
7. S. Kotha, S. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633 9695
8. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508 524
9. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 38 1999 2411 2413
10. M. Miyaura A. de Meijere, F.E. Diederich, Metal-catalyzed Cross-coupling Reactions 2nd ed. 2004 Wiley-VCH Weinheim 2419 2440
11. For reviews:
12. M. Seki J. Synth. Org. Chem., Jpn. 64 2006 853 866
13. M. Seki Synthesis 2006 2975 2992
14. F.-X. Felpin, T. Ayad, and S. Mitra Eur. J. Org. Chem. 2006 2679 2690
15. H. Sajiki, T. Kurita, A. Kozaki, G. Zhang, Y. Kitamura, T. Maegawa, and K. Hirota J. Chem. Res. 2004 593 595 [Erratum: J. Chem. Res. 2005, 344]
16. H. Sajiki, T. Kurita, A. Kozaki, G. Zhang, Y. Kitamura, T. Maegawa, and K. Hirota Synthesis 2005 537 542 [Erratum: Synthesis. 2005, 852]
17. H. Sajiki, G. Zhang, Y. Kitamura, T. Maegawa, and K. Hirota Synlett 2005 619 622 [Erratum: Synlett 2005, 1046]
18. T. Maegawa, Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi, K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, and H. Sajiki Chem. - Eur. J. 13 2007 5937 5943
19. Y. Kitamura, A. Sakurai, T. Udzu, T. Maegawa, Y. Monguchi, and H. Sajiki Tetrahedron 63 2007 10596 10602
20. T. Kurita, M. Abe, T. Maegawa, Y, Monguchi, and H. Sajiki Synlett 2007 2521 2524
21. Y. Kitamura, S. Sako, T. Udzu, A. Tsutsui, T. Maegawa, Y. Monguchi, and H. Sajiki Chem. Commun. 2007 5069 5071
22. S. Mori, T. Yanase, T. Aoyagi, Y. Monguchi, T. Maegawa, and H. Sajiki Chem. - Eur. J. 14 2008 6994 6999
23. Y. Kitamura, S. Sako, A. Tsutsui, Y. Monguchi, T. Maegawa, Y. Kitade, and H. Sajiki Adv. Synth. Catal. 352 2010 718 730
24. H. Sajiki, T. Ikawa, and K. Hirota Org. Lett. 6 2004 4977 4980
25. Y. Monguchi, K. Kitamoto, T. Ikawa, T. Maegawa, and H. Sajiki Adv. Synth. Catal. 350 2008 2767 2777
26. Y. Monguchi, T. Takahashi, Y. Iida, Y. Fujiwara, Y. Inagaki, T. Maegawa, and H. Sajiki Synlett 2008 2291 2294
27. G.P. Roth, and V. Farina Tetrahedron Lett. 36 1995 2191 2194
28. 3:
29. A.V. Coelho, A.L.F. Souza, P.G. Lima, J.L. Wardell, and O.A.C. Antunes Tetrahedron Lett. 48 2007 7671 7674 for Pd/MCM-41
30. S. Jana, S. Haldar, and S. Koner Tetrahedron Lett. 50 2009 4820 4823
31. 2/g, respectively.
32. 4 catalysis in PEG-400, see: W.-J. Zhou, K.-H. Wang, and J.-X. Wang J. Org. Chem. 74 2009 5599 5602
33. A.F. Littke, L. Schwarz, and G.C. Fu J. Am. Chem. Soc. 124 2002 6343 6348
34. G.A. Grasa, and S.P. Nolan Org. Lett. 3 2001 119 122
35. A.G. Martnez, J.O. Barcina, A.F. Cerezo, and L.R. Subramanian Synlett 12 1994 1047 1048
36. E. Fouquet, M. Pereyre, and A.L. Rodriguez J. Org. Chem. 62 1997 5242 5243
37. A. bele, K. Rubina, M. Fleisher, J. Popelis, P. Arsenyan, and E. Lukevics Appl. Organomet. Chem. 16 2002 141 147
38. S.P.H. Mee, V. Lee, and J.E. Baldwin Angew. Chem., Int. Ed. 43 2004 1132 1136
39. A. Ariafard, and B.F. Yates J. Am. Chem. Soc. 131 2009 13981 13991
40. W.J. Scott, and J.K. Stille J. Am. Chem. Soc. 108 1986 3033 3040
41. 3-catalyzed cross-coupling between 4-phenyl-1-oxycyclohexene and vinyltributyltin in NMP was likely to be impeded in the presence of LiCl, see V. Farina, and B. Krishnan J. Am. Chem. Soc. 113 1991 9585 9595
42. Since generated organotin residue made it very difficult to monitor the consumption of bromobenzene derivatives, the reaction time was fixed at 24 h for the following investigation.
43. The cross-coupling of 3-nitroiodobenzene afforded better yield of the desired biphenyl than that of 2- or 4-substituted iodobenzene probably due to the deiodination from the latter one, which is highly active. The cross-coupling of 4-cyanoiodobenzene at 50 °C gave the corresponding biphenyl in 80% yield, indicating almost no difference in the reactivity arisen from the substitution pattern. The slightly higher reactivity of 4-methoxyiodobenzene over 2- or 4-substituted one would be attributed to the poorer electron density at the 1-position that facilitates the oxidation addition to the palladium metal.
44. T. Ikawa, H. Sajiki, and K. Hirota Tetrahedron Lett. 60 2004 6189 6195
45. I.W. Davies, L. Matty, D.L. Hughes, and P.J. Reider J. Am. Chem. Soc. 123 2001 10139 10140
46. D.A. Conlon, B. Pipik, S. Ferdinand, C.R. LeBlond, J.R. Sowa, Izzo Jr., P. Collins, G.-J. Ho, J.M. Williams, Y.-J. Shi, and Y. Sun B Adv. Synth. Catal. 345 2003 931 935
47. R.G. Heidenreich, J.G.E. Kurauter, J. Pietsch, and K. Köhler J. Mol. Catal. A: Chem. 182-183 2002 499 509
48. K. Köhler, R.G. Heidenreich, J.G.E. Kurauter, and J. Pietsch Chem. - Eur. J. 8 2002 622 631
49. M. Rottländer, and P. Knochel J. Org. Chem. 63 1998 203 208
50. R. Rodríguez, L. Liguori, A.M. Carrillo, and H. Bjørsvik J. Org. Chem. 70 2005 9591 9594
51. Z. Xi, Y. Zhou, and W. Chen J. Org. Chem. 73 2008 8497 8501
52. R. Cella, R.L.O.R. Cunha, A.E.S. Reis, D.C. Pimenta, C.F. Klitzke, and H.A. Stefani J. Org. Chem. 71 2006 244 250
53. S.E. Denmark, and C.R. Butler Org. Lett. 8 2006 63 66
54. A.R. Gholap, K. Venkatesan, R. Pasricha, T. Daniel, R.J. Lahoti, and K.V. Srinivasan J. Org. Chem. 70 2005 4869 4872
55. A. Fürstner, G. Seidel, D. Kremzow, and C.W. Lehmann Organometalilics 22 2003 907 909
56. G.A. Molander, B. Canturk, and L.E. Kennedy J. Org. Chem. 74 2009 973 980
57. S. Sase, M. Jaric, A. Metzger, V. Malakhov, and P. Knochel J. Org. Chem. 73 2008 7380 7382
58. H.A. Stephen, K.S. Ralph, F. Tenja, M.S. Lothar, and C. Ji-Hyun Appl. Catal., A; General 291 2005 238 246
59. R.C. Young, R.C. Mithchell, T.H. Brown, C.R. Ganellin, R. Griffiths, M. Jones, K.K. Rana, D. Saunders, I.R. Smith, N.E. Sore, and T.J. Wilks J. Med. Chem. 31 1988 656 671
60. J. Schatz Sci. Synth. 9 2002 287 422
61. G. Andrei, K. Christiane, M. Georg, and K. Paul Tetrahedron 32 2006 7521 7533
62. C.A. Fleckenestein, and H. Plenio J. Org. Chem. 73 2008 3236 3244