Transmetalation in the Suzuki-Miyaura coupling: The fork in the trail

Angewandte Chemie - International Edition

Volumn 52, Issue 29, 2013, Pages 7362-7370

  Lennox, Alastair J J ^a   Lloyd Jones, Guy C ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

boron; cross coupling; palladium; reaction mechanisms; transmetalation

Indexed keywords

C-C BOND FORMING REACTION; CROSS-COUPLINGS; DISCOVERY CHEMISTRIES; MANUFACTURING PROCESS; REACTION MECHANISM; REDUCTIVE ELIMINATION; SUZUKI-MIYAURA COUPLING; TRANSMETALATION;

BORON; CATALYSIS; TRANSITION METALS;

PALLADIUM;

BORON; BORON DERIVATIVE; PALLADIUM; TRANSITION ELEMENT;

CATALYSIS; CHEMISTRY; CROSS COUPLING; KINETICS; REACTION MECHANISMS; REVIEW; THERMODYNAMICS; TRANSMETALATION;

BORON; CROSS COUPLING; PALLADIUM; REACTION MECHANISMS; TRANSMETALATION;

BORON COMPOUNDS; CATALYSIS; KINETICS; PALLADIUM; THERMODYNAMICS; TRANSITION ELEMENTS;

EID: 84880095538     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301737     Document Type: Review

References (73)

1. Ag:, H. C. Brown, C. H. Snyder, J. Am. Chem. Soc. 1961, 83, 1002-1003
2. Mg:, K. Kondo, S.-I. Murahashi, Tetrahedron Lett. 1979, 20, 1237-1240
3. Zn:, M. Srebnik, Tetrahedron Lett. 1991, 32, 2449-2452
4. Al:, G. Giacomelli, R. Menicagli, A. M. Caporusso, L. Lardicci, J. Org. Chem. 1978, 43, 1790-1793
5. Sn:, T. A. George, M. F. Lappert, Chem. Commun. 1966, 463
6. Cu:, Y. Yamamoto, H. Yatagai, I. Moritani, J. Am. Chem. Soc. 1975, 97, 5606-5607
7. Cu:, H. C. Brown, G. A. Molander, J. Org. Chem. 1981, 46, 645-647
8. Hg:, A. D. Ainley, F. Challenger, J. Chem. Soc. 1930, 2171-2180
9. Hg:, D. S. Matteson, P. G. Allies, J. Organomet. Chem. 1973, 54, 35-50.
10. M. Butters, J. N. Harvey, J. Jover, A. J. J. Lennox, G. C. Lloyd-Jones, P. M. Murray, Angew. Chem. 2010, 122, 5282-5286
11. Angew. Chem. Int. Ed. 2010, 49, 5156-5160
12. C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836
13. H. G. Kuivila, J. F. Reuwer, Jr., J. A. Mangravite, Can. J. Chem. 1963, 41, 3081-3090
14. A. J. J. Lennox, G. C. Lloyd-Jones, Isr. J. Chem. 2010, 50, 664-674, and references cited therein.
15. N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437-3440
16. N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 866-867
17. N. Miyaura, K. Yamada, H. Suginome, A. Suzuki, J. Am. Chem. Soc. 1985, 107, 972-980
18. A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168
19. T. Moriya, N. Miyaura, A. Suzuki, Synlett 1994, 149-151
20. N. Miyaura, J. Organomet. Chem. 2002, 653, 54-57
21. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
22. C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2011, 17, 2492-2503
23. B. P. Carrow, J. F. Hartwig, J. Am. Chem. Soc. 2011, 133, 2116-2119
24. A. F. Schmidt, A. A. Kurokhtina, E. V. Larina, Russ. J. Gen. Chem. 2011, 81, 1573-1574
25. C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2012, 18, 6616-6625
26. C. Amatore, A. Jutand, G. Le Duc, Angew. Chem. 2012, 124, 1408-1411
27. Angew. Chem. Int. Ed. 2012, 51, 1379-1382.
28. E.-I. Negishi, S. Baba, J. Chem. Soc. Chem. Commun. 1976, 596b-597b
29. S. Baba, E.-I. Negishi, J. Am. Chem. Soc. 1976, 98, 6729-6731.
30. 3N induces a "head-to-tail" (deborylative Heck) coupling with some alkenyl boronate esters and aryl halides:, N. Miyaura, A. Suzuki, J. Organomet. Chem. 1981, 213, C 53 -C 56.
31. L. J. Goossen, D. Koley, H. L. Hermann, W. Thiel, J. Am. Chem. Soc. 2005, 127, 11102-11114
32. R. Glaser, N. Knotts, J. Phys. Chem. A 2006, 110, 1295-1304
33. J. Jover, N. Fey, M. Purdie, G. C. Lloyd-Jones, J. N. Harvey, J. Mol. Catal. A 2010, 324, 39-47
34. S. Kozuch, J. M. L. Martin, ACS Catal. 2011, 1, 246-253.
35. A. A. C. Braga, N. H. Morgon, G. Ujaque, F. Maseras, J. Am. Chem. Soc. 2005, 127, 9298-9307
36. A. A. C. Braga, N. H. Morgon, G. Ujaque, A. Lledõs, F. Maseras, J. Organomet. Chem. 2006, 691, 4459-4466
37. A. A. C. Braga, G. Ujaque, F. Maseras, Organometallics 2006, 25, 3647-3658
38. C. Sicre, A. A. C. Braga, F. Maseras, M. M. Cid, Tetrahedron 2008, 64, 7437-7443.
39. V. V. Grushin, H. Alper, Organometallics 1993, 12, 1890-1901.
40. C. A. Hutton, A. K. L. Yuen, Tetrahedron Lett. 2005, 46, 7899-7903
41. C. M. Nunes, A. L. Monteiro, J. Braz. Chem. Soc. 2007, 18, 1443-1447
42. A. O. Aliprantis, J. W. Canary, J. Am. Chem. Soc. 1994, 116, 6985-6986.
43. A. N. Cammidge, V. H. M. Goddard, H. Gopee, N. L. Harrison, D. L. Hughes, C. J. Schubert, B. M. Sutton, G. L. Watts, A. J. Whitehead, Org. Lett. 2006, 8, 4071-4074
44. B. Basu, K. Biswas, S. Kundu, S. Ghosh, Green Chem. 2010, 12, 1734-1738.
45. Y. Yamamoto, M. Takizawa, X.-Q. Yu, N. Miyaura, Angew. Chem. 2008, 120, 942-945
46. Angew. Chem. Int. Ed. 2008, 47, 928-931
47. M. A. Oberli, S. L. Buchwald, Org. Lett. 2012, 14, 4606-4609
48. K. L. Billingsley, S. L. Buchwald, Angew. Chem. 2008, 120, 4773-4776
49. Angew. Chem. Int. Ed. 2008, 47, 4695-4698.
50. G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, T. R. Verhoeven, J. Org. Chem. 1994, 59, 8151-8156.
51. K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461-470.
52. G. R. Rosa, Quim. Nova 2012, 35, 1052-1056
53. V. R. Lando, A. L. Monteiro, Org. Lett. 2003, 5, 2891-2894.
54. Analogous to for example, Ar-Si coupling:, S. E. Denmark, R. C. Smith, W.-T. T. Chang, Tetrahedron 2011, 67, 4391-4396.
55. A. J. J. Lennox, G. C. Lloyd-Jones, J. Am. Chem. Soc. 2012, 134, 7431-7441.
56. G. R. Dick, E. M. Woerly, M. D. Burke, Angew. Chem. 2012, 124, 2721-2726
57. Angew. Chem. Int. Ed. 2012, 51, 2667-2672, and references cited therein
58. overview:, G. A. Molander, B. Canturk, Angew. Chem. 2009, 121, 9404-9425
59. Angew. Chem. Int. Ed. 2009, 48, 9240-9261
60. G. A. Molander, S. R. Wisniewski, J. Am. Chem. Soc. 2012, 134, 16856-16868, and references cited therein.
61. J. Uenishi, J. M. Beau, R. W. Armstrong, Y. Kishi, J. Am. Chem. Soc. 1987, 109, 4756-4758
62. I. E. Markõ, F. Murphy, S. Dolan, Tetrahedron Lett. 1996, 37, 2507-2510.
63. G. Zou, Y. K. Reddy, J. R. Falck, Tetrahedron Lett. 2001, 42, 7213-7215
64. Y. Nishihara, H. Onodera, K. Osakada, Chem. Commun. 2004, 192-193
65. J. Z. Deng, D. V. Paone, A. T. Ginnetti, H. Kurihara, S. D. Dreher, S. A. Weissman, S. R. Stauffer, C. S. Burgey, Org. Lett. 2009, 11, 345-347.
66. G. C. Fu, A. F. Littke, C. Dai, J. Am. Chem. Soc. 2000, 122, 4020-4028.
67. S. W. Wright, D. L. Hageman, L. D. McClure, J. Org. Chem. 1994, 59, 6095-6097.
68. On closer inspection of experimental details, many such procedures include addition of a drop of water. Even if not, as discussed earlier (Scheme 2), generation of boronic acid anhydride (9 or linear polymers) can reversibly liberate water in the medium. However, also see:, J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
69. S. Darses, J.-P. Genêt, J.-L. Brayer, J.-P. Demoute, Tetrahedron Lett. 1997, 38, 4393-4396
70. B. Schmidt, R. Berger, Adv. Synth. Catal. 2013, 355, 463-476
71. B. Schmidt, S. Krehl, A. Kelling, U. Schilde, J. Org. Chem. 2012, 77, 2360-2367
72. P. Mastrorilli, N. Taccardi, R. Paolillo, V. Gallo, C. F. Nobile, M. Räisänen, T. Repo, Eur. J. Inorg. Chem. 2007, 4645-4652.
73. We note that boronic acids 5 c or boronates 6 c can alter the course of oxidative addition:, G. Espino, A. Kurbangalieva, J. M. Brown, Chem. Commun. 2007, 1742-1744. It is conceivable that additional transmetalation pathways, stemming directly from an assisted oxidative addition, may also need to be considered in certain cases.