Pd-catalyzed N-arylation of heteroarylamines

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3481-3484

  Yin, Jingjun ^a   Zhao, Matthew M ^a   Huffman, Mark A ^a   McNamara, James M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

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ARTICLE;

EID: 0013157111     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0265923     Document Type: Article

References (43)

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14. DPPP = 1,3-bis(diphenylphosphino)propane; BINAP = 2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl; DPPF = 1,1′-bis(diphenylphosphmo)-ferrocene.
15. Direct reaction of 2-aminothiazoles with highly activated aryl halides in refluxing PhOH or EtOH has been very limited in scope and often resulted in low yields in the absence of a 4-substituent on the thiazole. For examples, see: (a) Sarkar, B. R.; Pathak, B.; Dutta, S.; Lahiri, S. C. J. Ind. Chem. Soc. 1984, 61, 151.
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20. For a Cu-catalyzed example, see ref 2f.
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22. First developed by van Leeuwen: (a) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081.
23. For previous examples using Xantphos in Pd-catalyzed C-N bond forming reactions, see: (b) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789.
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33. It formed likely via exchange between the aryl group of ArBr bound to Pd and the phenyl group of Xantphos. For similar observations, see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694-3703.
34. (b) Reference 8f,g,i.
35. For a mechanistic study, see: (c) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
36. For other examples where the use of Xantphos provides better results than the use of BINAP or DPPF, see ref 8e-j.
37. For discussions of its unique trans-coordination to Pd. see: (a) Reference 8g.
38. (b) Guari, Y.; van Strijdonck, G. P. F.; Boele, M. D. K.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Eur. J. 2001, 7, 475.
39. (c) Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
40. In this work, we found that BINAP was a better ligand only for reactions between 2-halopyridines and 2-aminopyridine/pyrimidines.
41. 2 flash column to give a crude product. It was then sonicated in 3 mL of toluene-hexanes (1:1), filtered, and dried to give the pure product as a white solid (167 mg, 87%).
42. The exact role of water is unclear. One possibility is that it helped solubilize the inorganic base to increase the reaction rate.
43. For a discussion of the concentration effect, see ref 8g.