Mild Pd/Cu-catalyzed sila-sonogashira coupling of (hetero)aryl bromides with (hetero)arylethynylsilanes under PTC conditions

Synlett

Volumn 23, Issue 5, 2012, Pages 773-777

  Bellina, Fabio ^a   Lessi, Marco ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

alkynylsilanes; copper; di arylethynes; palladium; phase transfer catalysis; Sonogashira reaction

Indexed keywords

(HETERO)ARYL BROMIDE DERIVATIVE; (HETERO)ARYLETHYNYLSILANE DERIVATIVE; BROMINE DERIVATIVE; COPPER; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYNYLATION; CARBOXYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIMERIZATION; NUCLEOPHILICITY; OXIDATION; PHASE TRANSITION; REVIEW; SONOGASHIRA REACTION; SYNTHESIS;

EID: 84858075545     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290601     Document Type: Review

References (72)

1. Tour J M., Acc. Chem. Res. 2000 33 791
2. Pugh V J., Hu Q.-S, Zuo X, Lewis F D., Pu L, J. Org. Chem. 2001 66 6136
3. Hill D J., Mio M J., Prince R B., Hughes T S., Moore J S., Chem. Rev. 2001 101 3893
4. Bunz U H. F., Chem. Rev. 2000 100 1605
5. Jenny N M., Mayor M, Eaton T R., Eur. J. Org. Chem. 2011 4965
6. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 16 4467
7. Selected reviews:, Rossi R, Carpita A, Bellina F, Org. Prep. Proced. Int. 1995 27 127
8. Sonogashira K, In Metal-Catalyzed Reactions Diederich F Stang P J. Wiley-VCH New York 1998 203-229
9. Sonogashira K, J. Organomet. Chem. 2002 653 46
10. Negishi E, Anastasia L, Chem. Rev. 2003 103 1979
11. Nicolaou K C., Bulger P G., Sarlah D, Angew. Chem. Int. Ed. 2005 44 4442
12. Yin L, Liebscher J, Chem. Rev. 2007 107 874
13. Chinchilla R, Nájera C, Chem. Rev. 2007 107 874
14. Doucet H, Hierso J.-C, Angew. Chem. Int. Ed. 2007 46 834
15. Plenio H, Angew. Chem. Int. Ed. 2008 47 6954
16. McGlacken G P., Fairlamb I J. S., Eur. J. Org. Chem. 2009 4011
17. Pal M, Synlett 2009 2896
18. Cassar L, J. Organomet. Chem. 1975 93 253
19. Dieck H A., Heck F R., J. Organomet. Chem. 1975 93 259
20. For recent examples of Cassar-Heck alkynylation reactions, see:, Kawanami H, Matsushima K, Sato M, Ikushima Y, Angew. Chem. Int. Ed. 2007 46 5129
21. Shi S, Zhang Y, Synlett 2007 1843
22. Ljungdahl T, Bennur T, Dallas A, Emtenaes H, Maartensson J, Organometallics 2008 27 2490
23. Komáromi A, Tolnai G L., Novák Z, Tetrahedron Lett. 2008 49 7294
24. Lipshutz B H., Chung D W., Rich B, Org. Lett. 2008 10 3793
25. Carpita A, Ribecai A, Tetrahedron Lett. 2009 50 204
26. Bakherad M, Amin A H., Keinvanloo A, Bahramian B, Raeissi M, Tetrahedron Lett. 2010 51 5653
27. Saha D, Dey R, Ranu B C., Eur. J. Org. Chem. 2010 6067
28. de Carné-Carnavalet B, Archambeau A, Meyer C, Cossy J, Folléas B, Brayer J.-L, Demoute J.-P, Org. Lett. 2011 13 956
29. Prabakaran K, Khan F N., Jin J S., Tetrahedron Lett. 2011 52 2566
30. Mori A, Kawashima J, Shimada T, Suguro M, Hirabayshi K, Nishihara Y, Org. Lett. 2000 2 2935
31. Kobayashi K, Sugie A, Takahashi M, Masui K, Mori A, Org. Lett. 2005 7 5083
32. Crisp G T., Turner P D., Stephens K A., J. Organomet. Chem. 1998 570 219
33. Eberhard M R., Wang Z, Jensen C M., Chem. Commun. 2002 818
34. Herrmann W A., Böhm V P. W., Reisinger C P., J. Organomet. Chem. 1998 576 23
35. Alonso D A., Nájera C, Pacheco M C., Org. Lett. 2000 2 1283
36. Alonso D A., Nájera C, Pacheco M C., Tetrahedron Lett. 2002 43 9365
37. Alonso D A., Nájera C, Pacheco M C., Adv. Synth. Catal. 2003 345 1146
38. Alacid E, Alonso D A., Botella L, Nájera C, Pacheco M C., Chem. Rec. 2006 6 117
39. Selected papers on Sonogashira coupling reactions in ionic liquids:, Deshmukh R R., Rajagopal R, Srinivasan K V., Chem. Commun. 2001 1544
40. Fukuyama T, Shinmen M, Nishitani S, Sato M, Ryu I, Org. Lett. 2002 4 1691
41. Park S B., Alper H, Chem. Commun. 2004 1306
42. Gholap A R., Venkatesan K, Pasricha R, Daniel T, Lahoti R J., Srinivasan K V., J. Org. Chem. 2005 70 4869
43. Rahman M T., Fukuyama T, Ryu I, Suzuki K, Yinoemura K, Hughes P F., Nokihara K, Tetrahedron Lett. 2006 47 2703
44. Hierso J.-C, Boudon J, Picquet M, Meunier P, Eur. J. Org. Chem. 2007 583
45. de Lima P G., Antunes O A. C., Tetrahedron Lett. 2008 49 2506
46. Fukuyama T, Rahman Md T., Maetani S, Ryu I, Chem. Lett. 2011 40 1027
47. Kabalka G W., Wang L, Namboodiri V, Pagni R M., Tetrahedron Lett. 2000 41 5151
48. Erdélyi M, Gogoll A, J. Org. Chem. 2001 66 4165
49. Hay A S., J. Org. Chem. 1960 25 1275
50. Hay A S., J. Org. Chem. 1962 27 3320
51. Siemsen P, Livingston R C., Diederich F, Angew. Chem. Int. Ed. 2000 39 2632
52. Rossi R, Carpita A, Lezzi A, Tetrahedron 1984 40 2773
53. Shultz D, Gwaltney K P., Lee H, J. Org. Chem. 1998 63 4034
54. Pak J J., Weakley T J. R., Haley M M., J. Am. Chem. Soc. 1999 121 8182
55. Nishihara Y, Ikegashira K, Hirabayashi K, Ando J.-I, Mori A, Hiyama T, J. Org. Chem. 2000 65 1780
56. Yang C, Nolan S P., Organometallics 2002 21 1020
57. Mio M J., Kopel L C., Braun J B., Gadzikwa T L., Hull K L., Brisbois R G., Markworth C J., Grieco P A., Org. Lett. 2002 4 3199
58. Halbes U, Pale P, Tetrahedron Lett. 2002 43 2039
59. Li G, Wang X, Wang F, Tetrahedron Lett. 2005 46 8971
60. Sørensen U, Pombo-Villar E, Tetrahedron 2005 61 2697
61. Gil-Moltó J, Nájera C, Adv. Synth. Catal. 2006 348 1874
62. Sommer W J., Weck M, Adv. Synth. Catal. 2006 348 2101
63. Nishihara Y, Inoue E, Okada Y, Takagi K, Synlett 2008 3041
64. Nishihara Y, Inoue E, Ogawa D, Okada Y, Noyori S, Takagi K, Tetrahedron Lett. 2009 50 4643
65. Severin R, Reimer J, Doye S, J. Org. Chem. 2010 75 3518
66. Recently, a Pd-free, Cu-catalyzed sila-Sonogashira cross-coupling protocol involving aryl iodides was published:, Nishihara Y, Noyori S, Okamoto T, Suetsugu M, Iwasaki M, Chem. Lett. 2011 40 972
67. For a discussion on phase-transfer catalysis in cross-coupling reactions, see:, Dehmlow E W., In Aqueous-Phase Organometallic Catalysis 2nd ed. Cornils B Herrmann W A. Wiley-VCH Weinheim 2004 272
68. Mkosza M, Fedoryski M, ARKIVOC 2006 (iv) 7
69. Hundertmart T, Littke A F., Buchwald S L., Fu G C., Org. Lett. 2000 2 1729
70. See, for example:, Wuts P G. M., Greene T W., In Greene"s Protective Groups in Organic Synthesis 4th ed. John Wiley and Sons Hoboken 2007 928-929
71. For an example of protiodesilylation of alkynyltrimethylsilanes with NaOH under PTC conditions, see:, Roser J, Eberbach W, Synth. Commun. 1986 16 983
72. Recently, a classical Sonogashira cross-coupling protocol for the synthesis of compounds 3 was published:, Moulton B E., Whitwood A C., Duhme-Klair A K., Lynam J M., Fairlamb I J. S., J. Org. Chem. 2011 76 5320