P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Tetrahedron Letters

Volumn 53, Issue 29, 2012, Pages 3754-3757

  Wong, Shun Man ^a   So, Chau Ming ^a   Chung, Kin Ho ^a   Luk, Chi Him ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

P,N Type ligand; Palladium; Phosphine; Suzuki coupling; Trifluoroborate

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; BORIC ACID; CHLORIDE; PALLADIUM; PHOSPHINE DERIVATIVE; POTASSIUM;

ARTICLE; CATALYST; MOLECULAR STABILITY; NONHUMAN; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 84862187104     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.017     Document Type: Article

References (69)

1. A.O. King, and N. Yasuda R.D. Larsen, Organometallics in Process Chemistry 2004 Springer-Verlag Berlin Heidelberg 205 245
2. N. Miyaura Top. Curr. Chem. 219 2002 11
3. A. Suzuki D. Astruc, Modern Arene Chemistry 2002 Wiley-VCH Weinheim 53 106
4. A. Suzuki J. Organomet. Chem. 653 2002 54
5. A. de Meijere, and F. Diederich Metal-Catalyzed Cross-Coupling Reactions Vols. 1-2 2004 Wiley-VCH Weinheim
6. M. Beller, and C. Bolm Transition Metals for Organic Synthesis 2nd ed. Building Blocks and Fine Chemicals Vol. 1-2 2004 Wiley-VCH Weinheim
7. E. Nigeshi Handbook of Organopalladium for Organic Synthesis Vols. 1-2 2002 Wiley-Interscience
8. J. Tsuji Palladium Reagents and Catalysts 2nd ed. 2004 Wiley Chichester
9. L.X. Yin, and J. Liebscher Chem. Rev. 107 2007 133
10. J.-P. Corbet, and G. Mignani Chem. Rev. 106 2006 2651
11. A. Roglans, A. Pla-Quintana, and M. Moreno-Manas Chem. Rev. 106 2006 4622
12. L. Ackermann Modern Arylation Methods 2009 Wiley-VCH Weinheim
13. D.G. Hall Boronic Acids 2006 Wiley-VCH Weinheim
14. 3K salts, see: G.A. Molander, and B. Canturk Angew. Chem., Int. Ed. 48 2009 9240
15. G.A. Molander, and N.O. Ellis Acc. Chem. Res. 40 2007 275
16. For selected examples, see: E. Vedejs, R.W. Chapman, S.C. Fields, S. Lin, and M.R. Schrimpf J. Org. Chem. 60 1995 3020
17. G.A. Molander, and D.J. Cooper J. Org. Chem. 72 2007 3558
18. G.A. Molander, J. Ham, and B. Canturk Org. Lett. 9 2007 821
19. For recent selected examples from Molander's group, see: G.A. Molander, L.N. Cavalcanti, B. Canturk, P.S. Pan, and L.E. Kennedy J. Org. Chem. 74 2009 7364
20. Y.A. Cho, D.S. Kim, H.R. Ahn, B. Canturk, G.A. Molander, and J. Ham Org. Lett. 11 2009 4330
21. G.A. Molander, W. Febo-Ayala, and L. Jean-Gerard Org. Lett. 11 2009 3830
22. G.A. Molander, and L. Jean-Gerard J. Org. Chem. 74 2009 5446
23. S.D. Dreher, S.E. Lim, D.L. Sandrock, and G.A. Molander J. Org. Chem. 74 2009 3626
24. G.A. Molander, and L. Jean-Gerard J. Org. Chem. 74 2009 1297
25. G.A. Molander, and D.J. Cooper J. Org. Chem. 73 2008 3885
26. G.A. Molander, P.E. Gormisky, and D.L. Sandrock J. Org. Chem. 73 2008 2052
27. G.A. Molander, and P.E. Gormisky J. Org. Chem. 73 2008 7481
28. G.A. Molander, and D.L. Sandrock Org. Lett. 9 2007 1597
29. G.A. Molander, and F. Vargas Org. Lett. 9 2007 203
30. T.E. Barder, and S.L. Buchwald Org. Lett. 6 2004 2649
31. For recent selected examples: R. Abel, and V.K. Aggarwal Angew. Chem., Int. Ed. 48 2009 6289
32. H. Doucet Eur. J. Org. Chem. 2008 2013
33. G.W. Kabalka, L.-L. Zhou, and A. Naravane Tetrahedron Lett. 47 2006 6887
34. R.L. Harker, and R.D. Crouch Synthesis 2007 25
35. J. Wu, L. Zhang, and Y. Luo Tetrahedron Lett. 47 2006 6747
36. J. Wu, L. Zhang, and H.-G. Xia Tetrahedron Lett. 47 2006 1525
37. R. Cella, R.L.O.R. Cunha, A.E.S. Reis, D.C. Klitzke, and H.A. Stefani J. Org. Chem. 71 2006 244
38. G.W. Kabalka, and M. Al-Masum Tetrahedron Lett. 46 2005 6329
39. T.D. Quach, and R.A. Batey Org. Lett. 5 2003 4397
40. T.D. Quach, and R.A. Batey Org. Lett. 5 2003 1381
41. G.-H. Fang, Z.-J. Yan, and M.-Z. Deng Org. Lett. 6 2004 357
42. S. Darses, and J.-P. Genet Eur. J. Org. Chem. 2003 4313
43. R.K. Arvela, N.E. Leadbeater, T.L. Mack, and C.M. Kormos Tetrahedron Lett. 47 2006 217
44. For a review describing indolyl/imidazolyl phosphine ligands, see: A. Zapf, and M. Beller Chem. Commun. 2005 431
45. For selected amination references, see: M. Nishiyama, T. Yamamoto, and Y. Koie Tetrahedron Lett. 39 1998 617
46. M.R. Netherton, and G.C. Fu Org. Lett. 3 2001 4295
47. F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, and M. Beller Chem. Eur. J. 10 2004 2983
48. For a selected amination reference, see: J.P. Wolfe, H. Tomori, J.P. Sadighi, J. Yin, and S.L. Buchwald J. Org. Chem. 65 2000 1158
49. For a selected amination reference, see: N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553
50. For selected amination references, see: S. Urgaonkar, J.-H. Xu, and J.G. Verkade J. Org. Chem. 68 2003 8416
51. Ch.V. Reddy, J.V. Kingston, and J.G. Verkade J. Org. Chem. 73 2008 3047
52. For a pertinent review on aryl chloride couplings, see: A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176
53. For recent review on the development and application of bulky electron-rich phosphines for Pd-catalyzed cross-coupling reaction of aryl halides and sulfonates, see: A. Zapf, and M. Beller Chem. Commun. 2005 431 and references cited therein
54. For review, see: F.Y. Kwong, and A.S.C. Chan Synlett 2008 1440
55. Z. Weng, S. Teo, and T.S. Andy Hor Acc. Chem. Res. 40 2007 676 684
56. Z. Weng, S. Teo, L.L. Koh, and T.S. Andy Hor Organometallics 23 2004 4342
57. A. Scrivanti, V. Beghetto, U. Matteoli, S. Antonaroli, A. Marinib, and B. Crociani Tetrahedron 61 2005 9752
58. L.-C. Liang, P.-S. Chien, and M.-H. Huang Organometallics 24 2005 353
59. M. Guo, F. Jian, and R. He Tetrahedron Lett. 47 2006 2033
60. For indolyl scaffold ligands, see: C.M. So, C.P. Lau, and F.Y. Kwong Org. Lett. 9 2007 2795
61. C.M. So, C.H. Yeung, C.P. Lau, and F.Y. Kwong J. Org. Chem. 73 2008 7803
62. C.M. So, C.P. Lau, Z. Zhou, and F.Y. Kwong Angew. Chem., Int. Ed. 47 2008 6402
63. 2-P,N fashion to the palladium center, see: K.H. Chung, C.M. So, S.M. Wong, C.H. Luk, Z. Zhou, C.P. Lau, and F.Y. Kwong Chem. Commun. 48 2012 1967
64. K.H. Chung, C.M. So, S.M. Wong, C.H. Luk, Z. Zhou, C.P. Lau, and F.Y. Kwong Synlett 2012 doi:10.1055/s-0031-1290666
65. C.M. So, and F.Y. Kwong Chem. Soc. Rev. 40 2011 4963
66. W.K. Chow, C.M. So, C.P. Lau, and F.Y. Kwong Chem. Eur. J. 17 2011 6913
67. C.M. So, C.P. Lau, and F.Y. Kwong Chem. Eur. J. 17 2011 761
68. P.Y. Yeung, C.M. So, C.P. Lau, and F.Y. Kwong Angew. Chem. Int. Ed. 49 2010 8918
69. C.M. So, W.K. Chow, P.Y. Choy, C.P. Lau, and F.Y. Kwong Chem. Eur. J. 16 2010 7996