A P,N-Ligand for palladium-catalyzed ammonia arylation: Coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions

Angewandte Chemie - International Edition

Volumn 49, Issue 24, 2010, Pages 4071-4074

  Lundgren, Rylan J ^a   Peters, Brendan D ^a   Alsabeh, Pamela G ^a   Stradiotto, Mark ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Ammonia; Arylation; Homogeneous catalysis; N P ligands; Palladium

Indexed keywords

AIR-STABLE; ARYL CHLORIDE; ARYLATIONS; CHEMO-SELECTIVITY; CHEMOSELECTIVE; CROSS-COUPLINGS; HOMOGENEOUS CATALYSIS; N P LIGANDS; P ,N LIGANDS; P LIGANDS; ROOM TEMPERATURE;

AMMONIA; AROMATIC COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; PALLADIUM; REACTION KINETICS;

LIGANDS;

EID: 77953095511     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000526     Document Type: Article

References (55)

1. Selected recent examples: a) M. J. Pouy, L. M. Stanley, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 11312;
2. b) T. Nagano, S. Kobayashi, J. Am. Chem. Soc. 2009, 131, 4200;
3. c) H. Rao, H. Fu, Y. Jiang, Y. Zhao, Angew. Chem. 2009, 121, 1134;
4. Angew. Chem. Int. Ed. 2009, 48, 1114;
5. d) C. Zhou, F. Chen, D. Yang, X. Jia, L. Zhang, J. Cheng, Chem. Lett. 2009, 38, 708;
6. e) C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789;
7. Angew. Chem. Int. Ed. 2008, 47, 8661;
8. f) V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2008, 120, 5302;
9. Angew. Chem. Int. Ed. 2008, 47, 5224.
10. For reviews, see: Pd: a) J. F. Hartwig, Acc. Chem. Res 2008, 41, 1534;
11. b) D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438;
12. Angew. Chem. Int. Ed. 2008, 47, 6338;
13. c) S. L. Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23;
14. d) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131;
15. e) J. F. Hartwig in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, p. 107; Cu:
16. f) F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088;
17. Angew. Chem. Int. Ed. 2009, 48, 6954.
18. a) H. Xu, C. Wolf, Chem. Commun. 2009, 3035;
19. b) L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem. 2009, 74, 4542;
20. c) D. Wang, Q. Cai, K. Ding, Adv. Synth. Catal. 2009, 351, 1722;
21. d) Z. Guo, J. Guo, Y. Song, L. Wang, G. Zou, Appl. Organomet. Chem. 2009, 23, 150;
22. e) N. Xia, M. Taillefer, Angew. Chem. 2009, 121, 343;
23. Angew. Chem. Int. Ed. 2009, 48, 337;
24. f) J. Kim, S. Chang, Chem. Commun. 2008, 3052;
25. g) M. K. Elmkaddem, C. Fischmeister, C. M. Thomas, J.-L. Renaud, Chem. Commun. 2010, 46, 925.
26. Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 10028.
27. D. S. Surry, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 10354.
28. T. Schulz, C. Torborg, S. Enthaler, B. Schäffner, A. Dumrath, A. Spannenberg, H. Neumann, A. Börner, M. Beller, Chem. Eur. J. 2009, 15, 4528.
29. G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc 2009, 131, 11049.
30. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350;
31. Angew. Chem. Int. Ed. 2002, 41, 4176.
32. For a recent review, see : N. A. Afagh, A. K. Yudin, Angew. Chem. 2010, 122, 270;
33. Angew. Chem. Int. Ed. 2010, 49, 262.
34. J. F. Hartwig, Inorg. Chem. 2007, 46, 1936.
35. R. J. Lundgren, A. Sappong-Kumankumah, M. Stradiotto, Chem. Eur. J. 2010, 16, 1983.
36. a) Ligands L1 (Me-DalPhos) and L7 (Mor-DalPhos) are now commercially available from Strem Chemicals;
37. 3 gave superior results compared to 2 or 5 equivalents, and the [Pd]:L7 appeared to be less important with minimal differences observed when varying the ratio from 1.5 to 4.
38. S. M. Bromidge et al., J. Med. Chem. 2000, 43, 1123. See the full reference in the Supporting Information.
39. Attempts to cross-couple 2-chloropyridines or 8-chloroquinoline led to nearly exclusive diarylation.
40. a) Room temperature C-N coupling using ArOTs has been achieved recently with alternative amine coupling partners: T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848;
41. 7]
42. Electron-poor aryl tosylates led to significant amounts of the corresponding phenol, as did aryl triflates.
43. For selected reports on chemoselective amine cross-coupling, see: a) X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653;
44. b) M. R. Biscoe, T. E. Barder, S. L. Buchwald, Angew. Chem. 2007, 119, 7370;
45. Angew. Chem. Int. Ed. 2007, 46, 7232;
46. c) B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 13552.
47. 6]
48. 2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
49. 2-P,N)Pd species relevant to cross-coupling catalysis, see: A. G. Sergeev, T. Schulz, C. Torborg, A. Spannenberg, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 7731;
50. Angew. Chem Int. Ed. 2009, 48, 7595.
51. 2-P,C)Pd manner: a) C. M. So, Z. Zhou, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 6502;
52. Angew. Chem. Int. Ed. 2008, 47, 6402;
53. b) C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 8179;
54. Angew. Chem. Int. Ed 2008, 47, 8059.
55. 3), employing electronically activated substrates (benzoate or cyano).