Tandem suzuki-miyaura cross-coupling/dehydrobromination of 1,1-dibromoalkenes to alkynes with a cyclobutene-1,2-diylbis(imidazolium) salt as catalyst precursor

Synthesis

Volumn , Issue 15, 2010, Pages 2621-2625

  Rahimi, Alireza ^a   Schmidt, Andreas ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

biscarbene complex; Corey Fuchs reaction; imidazol 2 ylidene; N heterocyclic carbene

Indexed keywords

BIS-CARBENE; BORONIC ACID; CATALYST PRECURSORS; CYCLOBUTENE; DIBROMOALKENES; EFFICIENT CATALYSTS; IMIDAZOL; IMIDAZOLIUM; N-HETEROCYCLIC CARBENES; ONE POT; PALLADIUM ACETATE; POTASSIUM TERT-BUTOXIDE; STARTING MATERIALS; SUZUKI-MIYAURA;

ACETYLENE; ALDEHYDES; BUTENES; CARBON INORGANIC COMPOUNDS; CATALYSTS; ORGANOMETALLICS; PALLADIUM; PALLADIUM COMPOUNDS; TOLUENE;

SYNTHESIS (CHEMICAL);

1,1 DIBROMOALKENE; ALDEHYDE; ALKYNE DERIVATIVE; BORONIC ACID DERIVATIVE; CYCLOBUTENE 1,2 DIYLBIS(IMIDAZOLIUM); IMIDAZOLE DERIVATIVE; PALLADIUM ACETATE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL MODIFICATION; COREY FUCHS REACTION; DEHYDROBROMINATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION;

EID: 77954890338     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218848     Document Type: Article

References (59)

1. (a) Modern Acetylene Chemistry Stang P J. Diederich F VCH Weinheim 1995
2. (b) Acetylene Chemistry: Chemistry, Biology and Material Science Diederich F Stang P J. Tykwinski R R. Wiley-VCH Weinheim 2005
3. (a)Science of Synthesis Hopf H Thomas E Vol. 43 Thieme: Stuttgart 2008
4. (b)Methoden der Organischen Chemie, Houben-Weyl Vol.5/2a Müller E Thieme Stuttgart 1977
5. (a) Gleiter R, Merger R, In Modern Acetylene Chemistry Stang P J. Diederich E VCH Weinheim 1995 285
6. (b)Gleiter R, Angew. Chem., Int. Ed. Engl. 1992 31 27
7. Angew. Chem. 1992, 104, 29
8. (c)Krebs A, Wilke J, Top. Curr. Chem. 1983 109 189
9. (d)Nakagawa M, In The Chemistry of the Carbon-Carbon Triple Bond Patai S Wiley New York 1978 635
10. (a)Hopf H, Asian Chem. Lett. 2007 11 153
11. Kivala M, Diederich F, Pure Appl. Chem. 2008 80 411
12. Organic Electronic Materials Farchiono R Grosso G Springer Berlin 2001
13. ShiShun A L. K., Tykwinski R R., Angew. Chem. Int. Ed. 2006 45 1034
14. Angew. Chem. 2006, 118, 1050
15. (a)Sankararaman S, In Science of Synthesis Vol. 43 Hopf H Thomas E Thieme Stuttgart 2008 435
16. (b)Brandsma L, Preparative Acetylenic Chemistry, 2nd ed. Elsevier Amsterdam 1988
17. (c)Viehe H G., Chemistry of Acetylenes Marcel Dekker New York 1969
18. (d)Ben-Efraim D A., In The Chemistry of the Carbon-Carbon Triple Bond Patai S Wiley New York 1978 755
19. (a)Schobert R, Gordon G J., In Science of Synthesis Vol. 27 Padwa A Thieme Stuttgart 2004 973
20. (b)Corey E J., Fuchs P L., Tetrahedron Lett. 1972 3769
21. Ratovelomanana V, Rollin Y, Gëbëhenne C, Gosmini C, Përichon J, Tetrahedron Lett. 1994 35 4777
22. (a)Molander G A., Yokoyama Y, J. Org. Chem. 2006 71 2493
23. (b)Kabalka G W., Dong G, Venkataiah B, Tetrahedron Lett. 2005 46 763
24. (c)Bauer A, Miller M W., Susan F V., McCombie S W., Synlett 2001 254
25. (d)Shen W, Synlett 2000 737
26. (e)Roush W R., Reilly M L., Kayama K, Brown B B., J. Org. Chem. 1997 62 8708
27. (f)Baldwin J E., Chesworth R, Parker J S. P., Russel A T., Tetrahedron Lett. 1995 36 9551
28. (g)Roush W R., Moriarty K J., Brown B B., Tetrahedron Lett. 1990 31 6509
29. (h)Roush W R., Brown B B., Drozda S E., Tetrahedron Lett. 1988 29 3541
30. (a)Chelucci G, Capitta F, Baldino S, Pinna G A., Tetrahedron Lett. 2007 48 6514
31. (b)Chelucci G, Capitta F, Baldino S, Tetrahedron 2008 64 10250
32. (a)Jacobsen M F., Moses J E., Adlington R M., Baldwin J E., Org. Lett. 2005 7 641
33. (b)Jacobsen M F., Moses J E., Adlington R M., Baldwin J E., Tetrahedron 2006 62 1675
34. Shen W, Wang L, J. Org. Chem. 1999 64 8873
35. (a)Olivo H F., Velázquez F, Trevisan H C., Org. Lett. 2000 2 4055
36. (b)Trost B M., Dirat O, Gunzner J L., Angew. Chem. Int. Ed. 2002 41 841
37. Angew. Chem. 2002, 114, 869
38. (c)Trost B M., Gunzner J L., Dirat O, Rhee Y H., J. Am. Chem. Soc. 2002 124 10396
39. (d)Huang H, Panek J S., Org. Lett. 2004 6 4383
40. (e)Centonze-Audureau S, Porëe F.-H, Betzer J.-F, Brion J.-D, Pancrazi A, Ardisson J, Synlett 2005 981
41. (f)Arai N, Miyaoku T, Teruya S, Mori A, Tetrahedron Lett. 2008 49 1000
42. (a)Schmidt A, Münster N, Dreger A, Angew. Chem. Int. Ed. 2010 49 2790
43. Angew. Chem. 2010, 122, 2851
44. (b)Scherbakow S, Namyslo J C., Gjikaj M, Schmidt A, Synlett 2009 1964
45. (c)Schmidt A, Snovydovych B, Synthesis 2008 2798
46. (d)Schmidt A, Snovydovych B, Hemmen S, Eur. J. Org. Chem. 2008 4313
47. (e)Schmidt A, Beutler A, Albrecht M, Ramrez F J., Org. Biomol. Chem. 2008 6 287
48. (f)Schmidt A, Snovydovych B, Habeck T, Drttboom P, Gjikaj M, Adam A, Eur. J. Org. Chem. 2007 4909
49. (g)Schmidt A, Habeck T, Snovydovych B, Eisfeld W, Org. Lett. 2007 9 3515
50. Schmidt A, Rahimi A, Chem. Commun. 2010 46 2995
51. Desai N B., McKelvie N, Ramirez F, J. Am. Chem. Soc. 1962 84 1745
52. Bestmann H J., Frey H, Liebigs Ann. Chem. 1980 12 2061
53. Lok W N., Ward A D., Aust. J. Chem. 1978 31 617
54. Quesada E, Raw S A., Reid M, Roman E, Taylor R J. K., Tetrahedron 2006 62 6673
55. Lipshutz B H., Chung D W., Rich B, Org. Lett. 2008 10 3793
56. Moon J, Jang M, Lee S, J. Org. Chem. 2009 74 1403
57. Dhudshia B, Thadani A N., Chem. Commun. 2006 668
58. Savarin C, Srogl J, Liebeskind L S., Org. Lett. 2001 3 91
59. Wan C.-W, Burghart A, Chen J, Bergstroem F, Johansson L B.-A, Wolford M F., Kim T G., Topp M R., Hochstrasser R M., Burgess K, Chem. Eur. J. 2003 9 4430