Palladium-catalyzed Sonogashira coupling of aryl mesylates and tosylates

Chemistry - A European Journal

Volumn 16, Issue 33, 2010, Pages 9982-9985

  Choy, Pui Ying ^a   Chow, Wing Kin ^a   So, Chau Ming ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Alkynes; Cross coupling; Palladium phosphanes; Sonogashira coupling

Indexed keywords

ALKYNES; CROSS-COUPLINGS; FACILE ACCESS; ISOQUINOLINES; MESYLATES; SONOGASHIRA COUPLING;

ACETYLENE; PALLADIUM;

CHEMICAL REACTIONS;

ALKYNE; BENZENE DERIVATIVE; MESYLIC ACID DERIVATIVE; PALLADIUM; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKYNES; BENZENE DERIVATIVES; CATALYSIS; MESYLATES; PALLADIUM; STEREOISOMERISM; TOSYL COMPOUNDS;

EID: 77956105455     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001269     Document Type: Article

References (43)

1. F. Diederich, P. Stang, R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH: Weinheim, 2005.
2. For a Highlight and reviews, see: a) H. Plenio, Angew. Chem. 2008, 120, 7060;
3. Angew. Chem. Int. Ed. 2008, 47, 6954;
4. H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850;
5. Angew. Chem. Int. Ed. 2007, 46, 834;
6. R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874;
7. M. S. Viciu, S. P. Nolan, Arylation Reactions of Alkynes: The Sonogashira Reaction in Modern Arylation Methods (Ed.: L. Ackermann), Wiley-VCH, Weinheim, 2009, pp. 183-220.
8. For a review describing modular/coupling approaches in total synthesis, see: K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516;
9. Angew. Chem. Int. Ed. 2005, 44, 4442.
10. For examples of Sonogashira coupling without Cu cocatalyst, see: a) A. Tougerti, S. Negri, A. Jutand, Chem. Eur. J. 2007, 13, 666;
11. M. Ahlquist, P. O. Norrby, Organometallics 2007, 26, 550;
12. Y. Liang, Y.-X. Xie, J.-H. Li, J. Org. Chem. 2006, 71, 379;
13. C. Yi, R. Hua, J. Org. Chem. 2006, 71, 2535;
14. B. Liang, M. Dai, J. Chen, Z. Yang, J. Org. Chem. 2005, 70, 391;
15. S. Urgaonkar, J. G. Verkade, J. Org. Chem. 2004, 69, 5752.
16. For examples at room-temperature conditions, see: a) A. Soheili, J. Albaneze-Walker, J. A. Murry, P. G. Dormer, D. L. Hughes, Org. Lett. 2003, 5, 4191;
17. T. Hundertmark, A. F. Littke, S. L. Buchwald, G. C. Fu, Org. Lett. 2000, 2, 1729;
18. V. P. W. Böhm, W. A. Herrmann, Eur. J. Org. Chem. 2000, 3679.
19. For recent selected references, see: a) C. Torborg, J. Huang, T. Schulz, B. Schaeffner, A. Zapf, A. Spannenberg, A. Borner, M. Beller, Chem. Eur. J. 2009, 15, 1329;
20. A. Komáromi, Z. Novak, Chem. Commun. 2008, 4968;
21. C. A. Fleckenstein, H. Plenio, Chem. Eur. J. 2007, 13, 2701;
22. K. W. Anderson, S. L. Buchwald, Angew. Chem. 2005, 117, 6329;
23. Angew. Chem. Int. Ed. 2005, 44, 6173;
24. A. Köllhofer, T. Pullmann, H. Plenio, Angew. Chem. 2003, 115, 1086;
25. Angew. Chem. Int. Ed. 2003, 42, 1056.
26. 2O is a highly moisture sensitive liquid and usually sold in an ampule.
27. For activated vinyl tosylates, see: a) D. Steinhuebel, J. M. Baxter, M. Palucki, I. W. Davies, J. Org. Chem. 2005, 70, 10124;
28. X. Fu, S. Zhang, J. Yin, D. P. Schumacher, Tetrahedron Lett. 2002, 43, 6673;
29. J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642.
30. D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175;
31. Angew. Chem. Int. Ed. 2003, 42, 5993.
32. O. R'Kyek, M. Nazare, A. Lindenschmidt, M. Urmann, N. Halland, J. Alonso, WO2009003589, 2009.
33. From Strem chemicals catalogue 2008-2010.
34. For our previous developments on CM-phos and related indolylphosphines, see: a) C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem. 2008, 73, 7731;
35. C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2007, 9, 2795;
36. C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 8179;
37. Angew. Chem. Int. Ed. 2008, 47, 8059;
38. C. M. So, Z. Zhou, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 6502;
39. Angew. Chem. Int. Ed. 2008, 47, 6402;
40. C. M. So, H. W. Lee, C. P. Lau, F. Y. Kwong, Org. Lett. 2009, 11, 317;
41. F. Y. Kwong, CM. So, US patent 2009/0326243A1, 2009;
42. for a related indolylphosphine developed by Beller and co-workers, see: g) F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, M. Beller, Chem. Eur. J. 2004, 10, 2983.
43. Editorial note: for a similar paper on this subject, see: O. R'kyek, N. Halland, A. Lindenschmidt, J. Alonso, P. Lindemann, M. Urmann, M. Nazaré, Chem. Eur. J. 2010, DOI: 10.1002/chem.201001524.