Evaluation of alternative solvents in common amide coupling reactions: Replacement of dichloromethane and N,N-dimethylformamide

Green Chemistry

Volumn 15, Issue 3, 2013, Pages 596-600

  MacMillan, Donna S ^a   Murray, Jane ^b   Sneddon, Helen F ^c   Jamieson, Craig ^a   Watson, Allan J B ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b Sigma Aldrich   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874450375     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c2gc36900a     Document Type: Article

References (69)

1. A. Greenberg, C. M. Breneman and J. F. Liebman, The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Material Science, Wiley, New York, 2000
2. N. Sewald and H.-D. Jakubke, Peptides: Chemistry and Biology, Wiley-VCH Verlag GmbH, Weinheim, 2002
3. M. A. Fischbach C. T. Walsh Chem. Rev. 2006 106 3468
4. M. Funabashi Z. Yang K. Nonaka M. Hosobuchi Y. Fujita T. Shibata X. Chi S. G. Van Lanen Nat. Chem. Biol. 2010 6 581
5. M. Simonovic T. A. Steitz Biochim. Biophys. Acta 2009 1789 612
6. P. D. Bailey, I. D. Collier and K. M. Morgan, In Comprehensive Organic Functional Group Transformations, ed., A. R. Katritzky, O. Meth-Cohn, and, C. W. Rees, Pergamon, Cambridge, 1995, vol. 5, ch. 6
7. L. A. Carpino M. Beyermann H. Wenschuh M. Bienert Acc. Chem. Res. 1996 29 268
8. J. M. Humphrey A. R. Chemberlin Chem. Rev. 1997 97 2243
9. Y. S. Klausner M. Bodansky Synthesis 1972 453
10. F. Albericio R. Chinchilla D. J. Dodsworth C. Nájera Org. Prep. Proced. Int. 2001 33 203
11. P. Li J. C. Xu J. Pept. Res. 2001 58 129
12. D. T. Elmore Amino Acids, Pept. Proteins 2002 33 83
13. F. Albericio Curr. Opin. Chem. Biol. 2004 8 211
14. S.-Y. Han Y.-A. Kim Tetrahedron 2004 60 2447
15. C. A. G. N. Montalbetti V. Falque Tetrahedron 2005 61 10827
16. P. D. Bailey, T. J. Mills, R. Pettercrew and R. A. Price, in Comprehensive Organic Functional Group Transformations II, ed., A. R. Katritzky, and, R. J. K. Taylor, Elsevier, Oxford, 2005, vol. 5, ch. 7
17. J. W. Bode Curr. Opin. Drug. Discovery. Dev. 2006 9 765
18. E. Valeur M. Bradley Chem. Soc. Rev. 2009 38 606
19. A. El-Faham F. Albericio Chem. Rev. 2011 111 6557
20. V. R. Pattabiraman J. W. Bode Nature 2011 480 471
21. T. W. J. Cooper I. B. Campbell S. J. F. MacDonald Angew. Chem., Int. Ed. 2010 49 8082
22. S. D. Roughley A. M. Jordan J. Med. Chem. 2011 54 3451
23. J. A. Mitchell E. E. Reid J. Am. Chem. Soc. 1931 53 1879
24. B. S. Jursie Z. Zdravkovski Synth. Commun. 1993 23 2761
25. L. Perreux A. Loupy F. Volatron Tetrahedron 2002 58 2155
26. H. Charville D. Jackson G. Hodges A. Whiting Chem. Commun. 2010 46 1813
27. T. Maki K. Ishihara H. Yamamoto Tetrahedron 2007 63 8645
28. K. Ishihara S. Ohara H. Yamamoto J. Org. Chem. 1996 61 4196
29. P. Tang Org. Synth. 2005 81 262
30. K. Arnold B. Davies R. L. Giles C. Grosjean G. E. Smith A. Whiting Adv. Synth. Catal. 2006 348 813
31. K. Arnold A. S. Batsanov B. Davies A. Whiting Green Chem. 2008 10 124
32. R. M. Al-Zoubi O. Marion D. G. Hall Angew. Chem., Int. Ed. 2008 47 2876
33. K. Ishihara Tetrahedron 2009 65 1085
34. T. Marcelli Angew. Chem., Int. Ed. 2010 49 6840
35. P. Starkov T. D. Sheppard Org. Biomol. Chem. 2011 9 1320
36. C. Gunanathan Y. Ben-David D. Milstein Science 2007 317 790
37. L. U. Nordstrøm H. Vogt R. Madsen J. Am. Chem. Soc. 2008 130 17672
38. A. J. A. Watson A. C. Maxwell J. M. J. Williams Org. Lett. 2009 11 2667
39. S. C. Ghosh S. Muthaiah Y. Zhang X. Xu S. H. Hong Adv. Synth. Catal. 2009 351 2643
40. SciFinder, American Chemical Society, Search conducted November 19th 2012, 2012
41. R. K. Henderson C. Jiménez-González D. J. C. Constable S. R. Alston G. G. A. Inglis G. Fisher J. Sherwood S. P. Binks A. D. Curzons Green Chem. 2011 13 854
42. D. J. C. Constable C. Jiménez-González R. K. Henderson Org. Process Res. Dev. 2007 11 133
43. K. Alfonsi J. Colberg P. J. Dunn T. Fevig S. Jennings T. A. Johnson H. P. Kleine C. Knight M. A. Nagy D. A. Perry M. Stefaniak Green Chem. 2008 10 31
44. B. W. Cue J. Zhang Green Chem. Lett. Rev. 2009 2 193
45. D. S. MacMillan J. Murray H. F. Sneddon C. Jamieson A. J. B. Watson Green Chem. 2012 14 3016
46. A. El-Faham R. Subirós-Funosas R. Prohens F. Albericio Chem.-Eur. J. 2009 15 9404
47. A. El-Faham F. Albericio J. Org. Chem. 2008 73 27
48. R. Subirós-Funosas R. Prohens R. Barbas A. El-Faham F. Albericio Chem.-Eur. J. 2009 15 9394
49. http://www.sigmaaldrich.com/chemistry/chemical-synthesis/ technology-spotlights/comu.html
50. M. Junkers Aldrich ChemFiles 2010 10 1
51. N. L. Benoiton F. M. F. Chen J. Chem. Soc., Chem. Commun. 1981 543
52. M. Junkers Aldrich ChemFiles 2007 7.2 5
53. I. Abdelmoty F. Albericio L. A. Carpino B. M. Forman S. A. Kates Lett. Pept. Sci. 1994 1 57
54. M. Junkers Aldrich ChemFiles 2007 7.2 9
55. J. Coste D. Le Nguyen B. Castro Tetrahedron Lett. 1990 31 205
56. M. Junkers Aldrich ChemFiles 2007 7.2 8
57. H. Wissmann H.-J. Kleiner Angew. Chem., Int. Ed. Engl. 1980 19 133
58. R. Escher P. Bünning Angew. Chem., Int. Ed. Engl. 1986 25 277
59. http://www.archimica.com/pdf/archimica-t3p-brochure.pdf
60. http://www.archimica.com/pdf/archimica-t3p-datasheet.pdf
61. M. Junkers Aldrich ChemFiles 2007 7.2 11
62. www.sigmaaldrich.com
63. K. Watanabe N. Yamagiwa Y. Torisawa Org. Process Res. Dev. 2007 11 251
64. http://www.zeon.co.jp
65. R. Aul and B. Comanita, Manufacturing Chemist, May 2007, 33
66. J. Bian M. Xiao S. Wang Y. Lu Y. Meng Catal. Commun. 2009 10 1142
67. M. Winterberg, E. Schulte-Korne, U. Peters and F. Nierlich, Methyl tert-butyl ether, in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2010
68. V. Antonucci J. Coleman J. B. Ferry N. Johnson M. Mathe J. P. Scott J. Xu Org. Process Res. Dev. 2011 15 939
69. M. Nielsen H. Junge A. Kammer M. Beller Angew. Chem., Int. Ed. 2012 51 5711