Easily accessible and highly tunable Lndolyl phosphine ligands for suzuki-miyaura coupling of aryl chlorides

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2795-2798

  So, Chau Ming ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; INDOLE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; CHLORIDES; INDOLES; LIGANDS; PALLADIUM; PHOSPHINES;

EID: 34547203012     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070898y     Document Type: Article

References (46)

1. (a) de Meijere. A., Diederich, F., Eds. Metal-Catalyzed CrossCoupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
2. (b) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
3. (c) Nigeshi, E., Ed. Handbook of Organopalladium for Organic Synthesis; Wiley-Interscience: New York, 2002; Vols. 1 and 2.
4. (d) Tsuji, J. Palladium Reagents and Catalysts, 2nd ed.; Wiley: Chichester, 2004.
5. (e) Yin, L. X.; Liebscher, J. Chem. Rev. 2007, 107, 133.
6. (f) Corbet, J.-P.: Mignani, G. Chem. Rev. 2006, 106, 2651.
7. (g) Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622.
8. (h) Molander, G A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275.
9. (a) King, A. O.; Yasuda, N. In Organometallics in Process Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 2004; pp 205245.
10. (b) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
11. (c) Suzuki, A. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 53-106.
12. (d) Suzuki, A. J. Organomet. Chem. 2002, 653, 54.
13. For a pertinent review, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
14. For selected references, see: (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
15. (b) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
16. (c) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
17. (d) Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282.
18. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
19. For selected references, see: (a) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746.
20. (b) Kataoka. N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
21. For selected references, see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
22. (b) Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
23. (c) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
24. (d) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
25. (e) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc 2005, 127, 4685.
26. (f) Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484.
27. (g) Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
28. For selected references, see: (a) Zapf, A.; Jackstell, R.; Rataboul, F.; Reirmeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38.
29. (b) Harkal, S.; Rataboul, F.; Zapf, A.; Fuhrmann, C.; Reirmeier, T.; Monsees, A.; Beller, M. Adv. Synth. Catal. 2004, 346, 1742. Fora review, see:
30. (c) Zapf, A.; Beller, M. Chem. Commun. 2005, 431.
31. (a) Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
32. (b) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. J. Org. Chem. 1999. 64, 6797.
33. (a) Clarke, M. L.; Cole-Hamilton, D. J.; Woollins, J. D. J. Chem. Soc, Dalton Trans. 2001, 2721.
34. (b) Schareina, T.; Kempe, R. Angew. Chem., Int. Ed. 2002, 41, 1521.
35. (c) Cheng, J.; Wang, F.; Xu, J.-H.; Pan, Y.; Zhang, Z. Tetrahedron Lett. 2003, 44, 7095.
36. (d) Cho, S.-D.; Kim, H.-K.; Yim, H.-s.; Kim, M.-R.; Lee, J.-K.; Kim, J.-J.; Yoon, Y.-J. Tetrahedron 2007, 63, 1345.
37. Clarke, M. L.; Cole-Hamilton, D. J.; Slawin, A. M. Z.; Woollins, J. D. Chem. Commun. 2000, 2065.
38. (a) Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
39. (b) Urgaonkar. S.; Xu, J.-H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416.
40. (c) Kingston, J. V.; Verkade. J. G. J. Org. Chem. 2007, 72, 2816.
41. For reviews, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 233, 1.
42. (b) Urgaonkar, S.; Verkade, J. G. Specialty Chem. 2006, 26, 36.
43. There are no literature reports on the direct Fischer indolization in accessing 2′-substituted 2-arylindoles. Alternatively, these sterically hindered indole templates can be prepared by transition-metal-catalyzed coupling methods, from indole C-H activation (at the 2-position) with aryl halides.
44. 31P NMR when the solid-form ligand was allowed to stand either under air for 5 days or in solution-form for at least 5 days. In contrast, Pt-Bu3 has been shown to be destroyed in air within 2 h; see ref 7a.
45. For metal-arene π-interaction, see: (a) Reid, S. M.; Boyle, R. C.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2003, 125, 7816.
46. (b) Ref 7d.