Pd-catalyzed C-N bond formation with heteroaromatic tosylates

Chemistry - A European Journal

Volumn 16, Issue 18, 2010, Pages 5437-5442

  Mantel, Mette L H ^a   Lindhardt, Anders T ^a   Lupp, Daniel ^a   Skrydstrup, Troeis ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aryl tosylates; C n bond formation; Heterocycles; Heterogeneous catalysis; Palladium

Indexed keywords

AMIDATION; BOND FORMATION; BOND-FORMING REACTIONS; COUPLING REACTION; CYCLIC UREAS; HETEROCYCLES; HETEROGENEOUS CATALYSIS; NITROGEN BONDS; OXAZOLIDINONES; PRIMARY AMIDES; QUINOXALINES; RING SYSTEMS; SCALE-UP; STRUCTURAL DIVERSITY;

AMIDES; CATALYSIS; UREA;

PALLADIUM;

AMIDE; CARBON; CROSS LINKING REAGENT; HETEROCYCLIC COMPOUND; NITROGEN; PALLADIUM; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

AMIDES; CARBON; CATALYSIS; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM; STEREOISOMERISM; TEMPERATURE; TOSYL COMPOUNDS;

EID: 77951953084     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903235     Document Type: Article

References (53)

1. For reviews on Pd-catalyzed C-N bond formation, see: a) D. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438-6461;
2. Angew. Chem. Int. Ed. 2008, 47, 6338-6361;
3. b) L. Jiang, S. L. Buchwald in MetalCatalyzed Cross Coupling Reactions, Vol.2, 2nd ed. (Eds. : A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, pp. 699-760;
4. c) B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599-1626;
5. d) J. F. Hartwig in Handbook of Organopalladium Chemistry of Organic Synthesis, Vol.1 (Eds.: E.I. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 1051-1096;
6. e) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 279, 131-209;
7. f) D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041-2075;
8. g) J.F. Hartwig in Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, New York, 2000, pp. 195-262;
9. h) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125-146;
10. i) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818;
11. j) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860;
12. k) C. G. Frost, P. J. Mendona, Chem. Soc. Perkin Trans. 1 1998, 2615-2623.
13. a) G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 11049-11061;
14. b)T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848-13849;
15. c) X. H. Huang, K. W Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653-6655;
16. d) B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370.
17. For an example of amidation of enol tosylates, see A. Klapars, K. R. Campos, C. Chen, R. P. Volante, Org. Lett. 2005, 7, 1185-1188.
18. a) H. J. Roth, A. Kleemann, Pharmaceutical Chemistry: Drug Synthesis, , Vol.1, Wiley, New York, 1988;
19. b) F. Sha, X. Huang, Angew. Chem. 2009, 121, 3510-3513;
20. Angew. Chem. Int. Ed. 2009, 48, 3458-3461;
21. c) M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc. 2007, 129, 10096-10097;
22. d) A.S. Karpov, E. Merkul, F. Rominger, T. J. J. Muller, Angew. Chem. 2005, 117, 7112-7117;
23. Angew. Chem. Int. Ed. 2008, 44, 6951-6956;
24. e) M. C. Bagley, C. Glover, E. A. Merritt, Synlett 2007, 2459-2482;
25. f) M. D. Hill, M. Movassaghi, Chem. Eur. J. 2008, 14, 6836-6844;
26. g) A. Ghosh, J. E. Sieser, M. Riou, W. L. Cai, L. Rivera-Ruiz, Org. Lett. 2003, 5, 2207-2210. For some recentexamples of C-N bond formation with heteroaromatic systems,
27. see h) G. B. W. L. Ligthart, H. Ohkawa, R. P. Sijbesma, E. W. Meijer, J. Org. Chem. 2006, 71, 375-378;
28. i) Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7734-7735;
29. j) Q. Shen, T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 6586-6596;
30. k) B. P. Fors, K. Dooleweerdt, Q. Zeng, S. L. Buchwald, Tetrahedron 2009, 65, 6576-6583.
31. T. M. Gogsig, A. T. Lindhardt, M. Dekhane, J. Grouleff, T. Skrydstrup, Chem. Eur. J. 2009, 15, 5950-5955.
32. T. M. Gogsig, A. T. Lindhardt, T. Skrydstrup, Org. Lett. 2009, 11, 4886-4888.
33. DPPF = l,l′-bis(diphenylphosphino)ferrocene, DPPP=l,3- bis(diphenylphosphino)propane, DPPE = ethylenebis(diphenylphosphine), DPPPe = l,5-bi.s(diphenylphosphino)pentane, BINAP = 2,2′-bis(diphenylphosphino)-l, l′-binaphthalene, BDPPP=bis(2-diphenylphosphinophenylether), DiPrPF = 1,1′ -bis(ditsopropylphosphino)ferrocene, DitBuPF=1.1′ -bis(ditertbutylphosphino)ferrocene. PPFPtBu = (2R)-l-[(lR)-l-[bis(l,l.- dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene.
34. For a recent example of efficient palladium-catalyzed N-arylations with secondary amides including relevant references, see J. D. Hicks, A. M. Hyde, A. B. Cuezva, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 16720-16734.
35. a) H. Prokopcová, C. O. Kappe, Angew. Chem, 2009, 121, 2312-2322;
36. Angew. Chem. Int. Ed. 2009, 48, 2276-2286;
37. b) H. Li, H. Yang, L. S. Liebeskind, Org. Lett. 2008, 10, 4375-4378;
38. c) H. Yuo, H. Li, R. Wittenberg, M. Egi, W Huang, L. S. Liebeskind, J. Am. Chem. Soc. 2007, 129, 1132-1140.
39. For recent papers on the use of Xantphos with carbamates, see: a) A. A. Trabanco, J. A. Vega, M. A. Fernández, J. Org. Chem. 2007, 72, 8146-8148;
40. b) F. Shi, M. R. Smith III, R. E. Maleczka, Jr, Org. Lett. 2006, 8, 1411-1414;
41. c) J. Yin, S. L. Buchwald, Org. Lett. 2000, 2, 1101-1104.
42. a) S. R. Stauffer, S. Lee, J. P. Stambuli, S. I. Hauck, J. F. Hartwig, Org. Lett. 2000, 2, 1423-1426;
43. b) M, Prashad, X. Y. Mak, Y. Liu, O. Repic, J. Org. Chem. 2003, 68, 1163-1164;
44. c) K. W. Anderson, M. Mendez-Perez, J. Priego, S. L. Buchwald, J. Org. Chem. 2003, 68, 9563-9573;
45. d) B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 13552-13554;
46. e) J. K. Laha, P. Petrou, G. D. Cuny, J. Org. Chem. 2009, 74, 3152-3155.
47. a) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J Org. Chem, 1999, 64, 5575-5580;
48. b) G. A. Grasa, M. S. Viciu, J. Huang, S. P. Nolan, J. Org. Chem. 2001, 66, 7729-7737;
49. c) L. Ackermann, Org. Lett. 2005, 7, 439-442;
50. d) I, P. Beletskaya, V. I. Bregadze, K. Z. Kabytaev, G. G. Zhigareva, P. V. Petrovskii, I. V Glukhov, Z. A. Starikova, Organometallics 2007, 26, 2340-2347.
51. S. Kramer, K. Dooleweerdt, A. T. Lindhardt, M. Rottlander, T. Skrydstrup, Org. Lett. 2009, 11, 4208-4211.
52. For examples on the use of Josiphos ligands with aromatic tosylates, see reference [2b] and a) M. E. Limmert, A. H, Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364-9370;
53. b) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 8704-8705, and references therein.