Practical one-pot preparation of magnesium Di(hetero)aryl- and magnesium dialkenylboronates for Suzuki-Miyaura cross-coupling reactions

Angewandte Chemie - International Edition

Volumn 50, Issue 32, 2011, Pages 7290-7294

  Haag, Benjamin A ^a   Sämann, Christoph ^a   Jana, Anukul ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

boron; boronate; cross coupling; magnesium; palladium

Indexed keywords

ALKENYL; ARYL GROUP; BORONATE; CROSS-COUPLINGS; FUNCTIONALIZED; ONE POT; ONE-POT SYNTHESIS; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

BORON; BORON COMPOUNDS; BROMINE COMPOUNDS; MAGNESIUM;

CHEMICAL REACTIONS;

EID: 79960922026     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103022     Document Type: Article

References (60)

1. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633
2. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
3. S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676
4. Angew. Chem. Int. Ed. 2001, 40, 4544
5. A. Suzuki, Heterocycles 2010, 80, 15
6. A. Suzuki, J. Organomet. Chem. 1999, 576, 147
7. Boronic Acids (Ed.:, D. G. Hall,), Wiley-VCH, Weinheim, 2005
8. N. Miyaura, in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, p. 41
9. N. Miyaura, in Cross-Coupling Reactions-A Practical Guide (Ed.:, N. Miyaura,), Springer, New York, 2002, p. 11
10. C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027
11. L. Ackermann, R. Born, Angew. Chem. 2005, 117, 2497
12. Angew. Chem. Int. Ed. 2005, 44, 2444
13. L. Ackermann, Synlett 2007, 507.
14. N. Miyaura, A. Suzuki, Synth. Commun. 1981, 11, 513
15. T. Ohe, N. Miyaura, A. Suzuki, J. Org. Chem. 1993, 58, 2201
16. D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170
17. A. Zapf, M. Beller, Chem. Eur. J. 2000, 6, 1830.
18. G. A. Molander, B. Canturk, Angew. Chem. 2009, 121, 9404
19. Angew. Chem. Int. Ed. 2009, 48, 9240
20. A. Darses, J.-P. Genet, Chem. Rev. 2008, 108, 288
21. G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275.
22. D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961
23. E. P. Gillis, M. D. Burke, Aldrichimica Acta 2009, 42, 17
24. E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2007, 129, 6716.
25. H. Noguchi, K. Hojo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 758
26. H. Noguchi, T. Shioda, C.-M. Chou, M. Suginome, Org. Lett. 2008, 10, 377
27. N. Iwadate, M. Suginome, Org. Lett. 2009, 11, 1899.
28. D. D. Winkle, K. M. Schaab, Org. Process Res. Dev. 2001, 5, 450
29. A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988
30. D. S. Matteson, Reactivity and Structure Concept in Organic Synthesis: Stereodirected Synthesis with Organoboranes, Vol. 32, Springer, New York, 1994
31. M. Vaultier, B. Carboni, in Comprehensive Organometallic Chemistry, Vol. 11 (Eds.:, G. Wilkinson, F. G. Stone, E. W. Abel,), Pergamon, New York, 1995, p. 191
32. K. Smith, A. Pelter, in Comprehensive Organic Synthesis, Vol. 8 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, New York, 1991, p. 703
33. M. Zaidlewicz, M. Krzeminski, Sci. Synth. 2004, 6, 1097
34. M. M. Midland, Chem. Rev. 1989, 89, 1553
35. C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415
36. V. Darmency, P. Renaud, Top. Curr. Chem. 2006, 263, 71.
37. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890
38. C. Kleeberg, L. Dang, Z. Lin, T. B. Marder, Angew. Chem. 2009, 121, 5454
39. Angew. Chem. Int. Ed. 2009, 48, 5350
40. L. Dang, Z. Lin, T. B. Marder, Chem. Commun. 2009, 3987.
41. E. Demory, V. Blandin, J. Einhorn, P. Y. Chavant, Org. Process Res. Dev. 2011, 15, 710.
42. B. M. Trost, Angew. Chem. 1995, 107, 285
43. Angew. Chem. Int. Ed. Engl. 1995, 34, 259
44. B. M. Trost, Science 1991, 254, 1471.
45. A patent application has been filed.
46. R.-S., Gan, T. S. Hor in Ferrocenes, (Eds.:, A. Togni, T. Hayashi,), VCH, Weinheim, 1995, p. 1-104
47. G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107
48. G. A. Molander, C.-S. Yun, M. Ribagorda, B. Biolatto, J. Org. Chem. 2003, 68, 5534.
49. F. M. Piller, A. Metzger, M. A. Schade, B. A. Haag, A. Gavryushin, P. Knochel, Chem. Eur. J. 2009, 15, 7192.
50. 2MgX only reflects the stoichiometry used.
51. J. Högermeier, H.-U. Reissig, Chem. Eur. J. 2007, 13, 2410
52. J. Dash, T. Lechel, H.-U. Reissig, Org. Lett. 2007, 9, 5541
53. J. B. Grimm, K. J. Wilson, D. J. Witter, J. Org. Chem. 2009, 74, 6390.
54. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954
55. L. Zhang, T. Meng, J. Wu, J. Org. Chem. 2007, 72, 9346
56. D. Zim, V. R. Lando, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049.
57. A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020
58. G. A. Molander, C. R. Bernardi, J. Org. Chem. 2002, 67, 8424
59. G. A. Molander, C.-S. Yun, Tetrahedron 2002, 58, 1465.
60. This proved to be necessary in less than 10 % of all cases studied.