Direct B-alkyl Suzuki-Miyaura cross-coupling of trialkyl-boranes with aryl bromides in the presence of unmasked acidic or basic functions and base-labile protections under mild non-aqueous conditions

Advanced Synthesis and Catalysis

Volumn 351, Issue 3, 2009, Pages 415-422

  Wang, Bing ^a   Sun, Hui Xia ^a   Sun, Zhi Hua ^b   Lin, Guo Qiang ^a  

^a FUDAN UNIVERSITY   (China)

^b Shanghai Saijia Chemicals Co Ltd   (China)

Author keywords

Alkylation; Boranes; Cross coupling; Palladium; Suzuki Miyaura reaction

Indexed keywords

EID: 60849120130     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800630     Document Type: Article

References (82)

1. For a novel synthesis and SAR study of derrubone, see: J. M. Hastings, M. K. Hadden, S. J. B. Blagg, J. Org. Chem. 2008, 73, 369.
2. For reviews, see: a) C. C. Price, Org. React. 1946, 3, 1;
3. b) G. A. Olah, R. Krishnamurthi, G. K. Surya, in: Comprehensive Organic Synthesis, 1st edn., Vol. 3, (Eds.: B. M. Trost, I. Fleming, G. Pattenden), Pergamon Press, Oxford, 1991, pp293;
4. c) R. M. Roberts, A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, 1st edn., Marcel Dekker, New York, 1984.
5. For reviews, see: a) P. H. Gore, Chem. Rev. 1955, 55, 229;
6. b) P. Metivier, in: Friedel-Crafts Acylation, 1st edn., (Eds.: R. A. Sheldon, H. Bekkum), Wiley-VCH, Weinheim, 2001.
7. Clemmensen reduction: a) E. Vedejs, Org. React. 1975, 22, 401;
8. hydrogenation-hydrogenolysis: b) W. H. Hartung, R. Simonoff, Org. React. 1953, 7, 263;
9. c) R. L. Augustine, Catalytic Hydrogenation, 1st edn., Marcel Dekker, New York, 1965; Wolff-Kishner reduction:
10. d) D. Todd, Org. React 1948, 4, 378; silane reduction:
11. e) D. N. Kursanov, Z. N. Parnes, N. M. Loim, Synthesis 1974, 633.
12. a) N. Miyaura, T. Ishiyama, M. Ishikawa, A. Suzuki, Tetrahedron Lett. 1986, 27, 6369;
13. b) N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, A. Suzuki, J. Am. Chem. Soc. 1989, 111, 314.
14. For reviews, see: c) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
15. d) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676;
16. Angew. Chem. Int. Ed. 2001, 40, 4544;
17. e) N. Miyaura, in: Metal-Catalyzed Cross-Coupling Reactions, 2nd edn., (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
18. For reviews, see: a) E. Negishi, Acc. Chem. Res. 1982, 15, 340;
19. b) E. Erdik, Tetrahedron 1992, 48, 9577;
20. c) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117;
21. d) E. Negishi, in: Handbook of Organopalladium Chemistry for Organic Synthesis, 1st edn., (Ed.: E. Negishi), John Wiley & Sons Inc., New York, 2002;
22. e) E. Negishi, X. Zeng, Z. Tan, M. Qian, Q. Hu, Z. Huang, in: Metal-Catalyzed Cross-Coupling Reactions, 2nd edn., (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
23. For reviews, see: a) J. K. Stille, Angew. Chem. 1986, 98, 504;
24. b) V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1;
25. c) M. Kosugi, K. Fugami, in: Handbook of Organopalladium Chemistry for Organic Synhesis, 1st edn., (Ed.: E. Negishi), John Wiley & Sons Inc., New York, 2002;
26. d) P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808;
27. Angew. Chem. Int. Ed. 2004, 43, 4704.
28. a) D. S. Matteson, Tetrahedron 1989, 45, 1859;
29. b) J. A. Marshall, B. A. Johns, J. Org. Chem. 1998, 63, 7885;
30. c) J. A. Soderquist, J. C. Justo de Pomar, Tetrahedron Lett. 2000, 41, 3537.
31. For leading references, see: a) G. A. Molander, T. Ito, Org. Lett. 2001, 3, 393;
32. b) G. A. Molander, C.-S. Yun, M. Ribagorda, B. Biolatto, J. Org. Chem. 2003, 68, 5534.
33. For excellent reviews of potassium organotrifluoroborates, see: c) G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275;
34. d) S. Darses, J.-P. Genet, Chem. Rev. 2008, 108, 288.
35. a) G. Zou, Y. K. Reddy, J. R. Falck, Tetrahedron Lett. 2001, 42, 7213;
36. b) G. A. Molander, C.-S. Yun, Tetrahedron 2002, 58, 1465;
37. c) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553. For the first example of Suzuki coupling using alkylboronic acid, see:
38. d) Y. Q. Mu, R. A. Gibbs, Tetrahedron Lett. 1995, 36, 5669.
39. Suzuki coupling using alkylboronates: e) M. Sato, N. Miyaura, A. Suzuki, Chem. Lett. 1989, 1405;
40. f) M. B. Andrus, C. Song, Org. Lett. 2001, 3, 3761.
41. Ate-complex of boronate: g) G. Zou, J. R. Falck, Tetrahedron Lett. 2001, 42, 5817.
42. Trialkylboranes were conveniently prepared from the corresponding Grignard reagents with boron trifluoride etherate: a) H. C. Brown, U. S. Racherla, J. Org. Chem. 1986, 51, 427.
43. Selected applications of trialkylboranes: b) D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099;
44. c) W. Oppolzer, I. Rodriguez, C. Starkemann, E. Walther, Tetrahedron Lett. 1990, 31, 5019;
45. d) T. Ukon, T. Harada, Eur. J. Org. Chem. 2008, 4405.
46. a) T. Harada, T. Yoshida, A. Inoue, M. Takeuchi, A. Oku, Synlett 1995, 283;
47. b) S. J. O'Connor, K. J. Barr, L. Wang, B. K. Sorensen, A. S. Tasker, H. Sham, S.-C. Ng, J. Cohen, E. Devine, S. Cherian, B. Saeed, H. Zhang, J. Y. Lee, R. Warner, S. Tahir, P. Kovar, P. Ewing, J. Alder, M. Mitten, J. Leal, K. Marsh, J. Bauch, D. J. Hoffman, S. M. Sebti, S. H. Rosenberg, J. Med. Chem. 1999, 42, 3701;
48. c) T. Güngör, Y. Chen, R. Golla, Z. Ma, J. R. Corte, J. P. Northrop, B. Bin, J. K. Dickson, T. Stouch, R. Zhou, S. E. Johnson, R. Seethala, J. H. M. Feyen, J. Med. Chem. 2006, 49, 2440;
49. d) L. R. Marrison, J. M. Dickinson, I. J. S. Fairlamb, Bioorg. Med. Chem. Lett. 2002, 12, 3509;
50. e) I. J. S. Fairlamb, L. R. Marrison, J. M. Dickinson, F.-J. Lu, J.-P. Schmidt, Bioorg. Med. Chem. 2004, 12, 4285.
51. a) P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404;
52. b) R.W. Hoffmann, Synthesis 2006, 3531.
53. Suzuki coupling of boronic acids in the presence of acidic functions has been reported: a) Y. Gong, W. He, Org. Lett. 2002, 4, 3803;
54. b) K. W. Anderson, S. L. Buchwald, Angew. Chem. 2005, 117, 6329;
55. Angew. Chem. Int. Ed. 2005, 44, 6173.
56. G. Manolikakes, M. A. Schade, C. M. Hernandez, H. Mayr, P. Knochel, Org. Lett. 2008, 10, 2765.
57. L. H. Toporcer, R. E. Dessy, S. I. E. Green, J. Am. Chem. Soc. 1965, 87, 1236.
58. N. Morohashi, T. Kitahara, T. Arima, S. Tanaka, Y. Ohba, T. Hattori, Org. Lett. 2008, 10, 2845.
59. L. Zhu, S. H. Shabbir, M. Gray, V. M. Lynch, S. Sorey, E. V. Anslyn, J. Am. Chem. Soc. 2006, 128, 1222.
60. J. M. Herbert, Tetrahedron Lett. 2004, 45, 817.
61. M. Prieto, E. Zurita, E. Rosa, L. Munoz, P. Lloyd-Williams, E. Giralt, J. Org. Chem. 2004, 69, 6812.
62. a) N. Jaber, D. Gelman, H. Schumann, S. Dechert, J. Blum, Eur. J. Org. Chem. 2002, 1628. Triethylaluminum was also shown to couple with aryl bromides under the assistance of a stoichiometric amount of lanthanide, however, whether this system tolerated acidic functions was not revealed:
63. b) M. Shenglof, D. Gelman, G. A. Molander, J. Blum, Tetrahedron Lett. 2003, 44, 8593.
64. N. A. Bumagin, E. V. Luzikova, J. Organomet. Chem. 1997, 532, 271.
65. See, for example: M. R. Netherton, C. Dai, K. Neuschütz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099.
66. G. A. Molander, B. W. Katona, F. Machrouhi, J. Org. Chem. 2002, 67, 8416.
67. L. H. Toporcer, R. E. Dessy, S. I. E. Green, Inorg. Chem. 1965, 4, 1649.
68. a) T. Flessner, S. Doye, J. Prakt. Chem. 1999, 341, 186;
69. b) F. Lehmann, Synlett 2004, 2447.
70. K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461.
71. 3 as the base, see: F. Chu, E. E. Dueno, K. W. Jung, Tetrahedron Lett. 1999, 40, 1847.
72. 1H NMR of the partially purified mixture, while the other component has only aromatic protons. The latter was assigned as dimerization side product as it showed strong fluorescence and it was not reductive de-halogenation side product by comparison with an authentic sample.
73. a) B. J. Backes, J. A. Ellman, J. Am. Chem. Soc. 1994, 116, 11171;
74. b) J. A. Soderquist, I. Kock, M. E. Estrella, Org. Process Res. Dev. 2006, 10, 1076.
75. T. Oh-e, N. Miyaura, A. Suzuki, J. Org. Chem. 1993, 58, 2201.
76. W.-C. Shieh, J. A. Carlson, J. Org. Chem. 1992, 57, 379.
77. a) P. G. M. Wuts, T. W. Greene, Greene's Protective Groups in Organic Synthesis, 4th edn., John Wiley & Sons, Hoboken, NJ, 2007;
78. b) P. J. Kocienski, Protecting Groups, 3rd edn., Thieme, New York, 2005.
79. a) D. Brückner, F.-T. Hafner, V. Li, C. Schmeck, J. Telser, A. Vakalopoulos, G. Wirtz, Bioorg. Med. Chem. Lett. 2005, 15, 3611;
80. b) H. Bischoff, F.-T. Hafner, C. Schmeck, J. Telser, A. Vakalopoulos, G. Wirtz, M. Bauser, D. Brückner, M. Wuttke, WO Patent, 2004/ 039453 A2.
81. T. Sassa, G. Niwa, H. Unno, M. Ikeda, Y. Miura, Tetrahedron Lett. 1974, 3941.
82. CCDC 704508 contains the supplementary crystallography 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.