Efficient copper-catalyzed sonogashira couplings of aryl halides with terminal alkynes in water

Synlett

Volumn , Issue 5, 2011, Pages 702-706

  Yang, Daoshan ^a   Li, Bing ^a   Yang, Haijun ^a   Fu, Hua ^a   Hu, Liming ^b  

^a TSINGHUA UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

alkyne; copper; Sonogashira coupling; synthetic method; water

Indexed keywords

1,10 PHENANTHROLINE; ALKYNE DERIVATIVE; ARYLHALIDE DERIVATIVE; COPPER; HALIDE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; LIGAND BINDING; MOLECULAR INTERACTION; PROCESS DEVELOPMENT; REACTION OPTIMIZATION; SOLVENT EFFECT; SONOGASHIRA REACTION; SYNTHESIS; WATER ANALYSIS;

EID: 79952452311     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259542     Document Type: Article

References (58)

1. Beutler U, Mazacek J, Penn G, Schenkel B, Wasmuth D, Chimia 1996 50 154
2. Grissom J W., Gunawardena G U., Klingenberg D, Huang D, Tetrahedron 1996 52 6453
3. Anastasia L, Negishi E, Org. Lett. 2001 3 3111
4. Yang C, Nolan S P., Organometallics 2002 21 1020
5. Plenio H, Hermann J, Sehring A, Chem. Eur. J. 2000 6 1820
6. Alami M, Crousse B, Ferri F, J. Organomet. Chem. 2001 624 114
7. Batey R A., Shen M, Lough A J., Org. Lett. 2002 4 141
8. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 16 4467
9. Champbell I B., In Organocopper Reagent: A Practical Approach Taylor R J. K. Oxford University Press Oxford 1994 217
10. Chinchilla R, Njera C, Chem. Rev. 2007 107 874
11. Okuro K, Furuune M, Enna M, Miura M, Nomura M, J. Org. Chem. 1993 58 4716
12. Thathagar M B., Beckers J, Rothenberg G, Green Chem. 2004 6 215
13. Ma D, Liu F, Chem. Commun. 2004 1934
14. Li J.-H, Li J.-L, Wang D.-P, Pi S.-F, Xie Y.-X, Zhang M.-B, Hu X.-C, J. Org. Chem. 2007 72 2053
15. Li J.-H, Li J.-L, Wang D.-P, Pi S.-F, Xie Y.-X, Zhang M.-B, Hu X.-C, J. Org. Chem. 2007 72 2053
16. Carril M, Correa A, Bolm C, Angew. Chem. Int. Ed. 2008 47 4862
17. Wang L, Li P, Zhang Y, Chem. Commun. 2004 514
18. Beletskaya I P., Latyshev G V., Tsvetkov A V., Lukashev N V., Tetrahedron Lett. 2003 44 5011
19. Huang H, Jiang H, Chen K, Liu H, J. Org. Chem. 2008 73 9061
20. Organic Synthesis in Water Grieca P A. Blackie London 1998
21. Siskin M, Katritzky A R., Chem. Rev. 2001 101 825
22. Lindström U M., Chem. Rev. 2002 102 2741
23. Kobayashi S, Manabe K, Acc. Chem. Res. 2002 35 209
24. Akiya N, Savage P E., Chem. Rev. 2002 102 2725
25. DeSimone J M., Science 2002 297 799
26. Poliakoff M, Fitzpatrick J M., Farren T R., Anastas P T., Science 2002 297 807
27. Li C.-J, Chem. Rev. 2005 105 3095
28. Blackmond D G., Armstrong A, Coomber V, Wells A, Angew. Chem. Int. Ed. 2007 46 3798
29. Minakata S, Komatsu M, Chem. Rev. 2008 101 825
30. Teo Y.-C, Chua G.-L, Chem. Eur. J. 2009 15 3072
31. Teo Y.-C, Adv. Synth. Catal. 2009 351 720
32. Zhu X, Ma Y, Su L, Song H, Chen G, Liang D, Wan Y, Synthesis 2006 3955
33. Carril M, SanMartin R, Domínguez E, Chem. Soc. Rev. 2008 37 639; references cited therein
34. Sinou D, Adv. Synth. Catal. 2002 344 221
35. Lipshutz B H., Chung D W., Rich B, Org. Lett. 2008 10 3793
36. Guan J T., Weng T Q., Yu G.-A, Liu S H., Tetrahedron Lett. 2007 48 7129
37. Leadbeater N E., Marco M, Tominack B J., Org. Lett. 2003 5 3919
38. For recent reviews on copper-catalyzed cross-couplings, see:, Klapars A, Antilla J C., Huang X, Buchwald S L., J. Am. Chem. Soc. 2001 123 7727
39. Ma D, Cai Q, Acc. Chem. Res. 2008 41 1450
40. Kunz K, Scholz U, Ganzer D, Synlett 2003 2428
41. Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 42 5400
42. Beletskaya I P., Cheprakov A V., Coord. Chem. Rev. 2004 248 2337
43. Evano G, Blanchard N, Toumi M, Chem. Rev. 2008 108 3054
44. Monnier F, Taillefer M, Angew. Chem. Int. Ed. 2009 48 6954; and references cited therein
45. Chen G, Zhu X, Cai J, Wan Y, Synth. Commun. 2007 37 1355
46. Guan J T., Yu G.-A, Chen L, Weng T Q., Yuan J J., Liu S H., Appl. Organomet. Chem. 2009 23 75
47. Selected papers for copper-catalyzed cross-couplings in organic solvents, see:, Rao H, Fu H, Jiang Y, Zhao Y, J. Org. Chem. 2005 70 8107
48. Rao H, Jin Y, Fu H, Jiang Y, Zhao Y, Chem. Eur. J. 2006 12 3636
49. Jiang D, Fu H, Jiang Y, Zhao Y, J. Org. Chem. 2007 72 672
50. Guo X, Rao H, Fu H, Jiang Y, Zhao Y, Adv. Synth. Catal. 2006 348 2197
51. Zeng L, Fu H, Qiao R, Jiang Y, Zhao Y, Adv. Synth. Catal. 2009 351 1671
52. Lu J, Gong X, Yang H, Fu H, Chem. Commun. 2010 46 4172
53. Rao H, Fu H, JiangY, Zhao Y, Angew. Chem. Int. Ed. 2009 48 1114
54. Liu X, Fu H, Jiang Y, Zhao Y, Angew. Chem. Int. Ed. 2009 48 348
55. Copper-catalyzed cross-couplings in neatly aqueous medium, see:, Wang F, Fu H, Jiang Y, Zhao Y, Green Chem. 2008 10 452
56. Wang F, Fu H, Jiang Y, Zhao Y, Adv. Synth. Catal. 2008 350 1830
57. Li X, Yang D, JiangY, Fu H, Green Chem. 2010 12 1097
58. Yang D, Fu H, Chem. Eur. J. 2010 16 2366