Direct conversion of arylamines to pinacol boronates: A metal-free borylation process

Angewandte Chemie - International Edition

Volumn 49, Issue 10, 2010, Pages 1846-1849

  Mo, Fanyang ^a   Jiang, Yubo ^b   Qiu, Di ^a   Zhang, Yan ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

^b TONGJI UNIVERSITY   (China)

Author keywords

Aryl boronates; Borylation; Cross coupling; Diazo compounds; Sandmeyer reaction

Indexed keywords

ARYL AMINES; ARYLBORONATES; BORONATE; BORYLATION; CHEMICAL EQUATIONS; CROSS-COUPLINGS; DIAZO COMPOUNDS; DIRECT BORYLATION; DIRECT CONVERSION; GOOD YIELD; METAL CATALYSIS; PINACOLS; ROOM TEMPERATURE; SANDMEYER REACTION; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

CHEMICAL BONDS; CHEMICAL REACTIONS; TRANSITION METALS;

METAL REFINING;

ALKANONE; AMINE; BORON; PINACOLONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; BORON; BUTANONES; MOLECULAR STRUCTURE;

EID: 77749327481     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905824     Document Type: Article

References (85)

1. For reviews, see: a) A. Suzuki, Acc. Chem. Res. 1982, 15, 178;
2. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
3. c) A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 49-97;
4. d) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
5. e) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633;
6. f) N. Miyaura, J. Organomet. Chem. 2002, 653, 54;
7. g) T. Ishiyama, N. Miyaura, Chem. Rea 2004, 3, 271;
8. h) N. Miyaura, Bull. Chem. Soc. Jpn. 2008, 81,1535.
9. D. G. Hall, Boronic Acids, Wiley, New York, 2005.
10. a) H. C. Brown, M. Srebnik, T. E. Cole, Organometallics 1986, 5, 2300;
11. b) H. C. Brown, T. E. Cole, Organometallics 1983, 2,1316.
12. For a seminal publication, see: a) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508. For reviews, see:
13. b) T. Ishiyama, N. Miyaura, J. Synth. Org. Chem. Jpn. 1999, 57, 503;
14. c) T. Ishiyama, N. Miyaura,J. Organomet. Chem. 2000, 611, 392;
15. d) N. Miyaura in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Chichester, 2001, Chapter 3.
16. a) T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, Tetrahedron Lett. 1997, 38, 3447;
17. b) A. Giroux, Y. Han, P. Prasit, Tetrahedron Lett. 1997, 38, 3841;
18. c) D. M. Willis, R. M. Strongin, Tetrahedron Lett. 2000, 41, 8683;
19. d) A. C. Carbonnelle, J. Zhu, Org. Lett. 2000, 2, 3477;
20. e) K. Takahashi, J. Takagi, T. Ishiyama, N. Miyaura, Chem. Lett. 2000, 29, 126;
21. f) M.H. Todd, C. Abell, J. Comb. Chem. 2001, 3, 319;
22. g) T. Ishiyama, K. Ishida, N. Miyaura, Tetrahedron 2001, 57, 9813;
23. h) T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392;
24. i) A. Fürstner, G. Seidel, Org. Lett. 2002, 4, 541;
25. j) L. Zhu, J. Duquette, M. Zhang, J. Org. Chem. 2003, 68, 3729;
26. k) A. Giroux, Tetrahedron Lett. 2003, 44, 233;
27. K. Billingsley, T.E. Barder, S.L. Buchwald, Angew. Chem. 2007, 119, 5455;
28. Angew. Chem. Int. Ed. 2007, 46, 5359.
29. For Pd-catalyzed borylation reactions that employ pinacolborane, see: a) M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458;
30. b) M. Murata, T. Oyama, S. Watanbe, Y. Masuda, J. Org. Chem. 2000, 65, 164;
31. c) O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2000, 65, 9268;
32. d) P. E. Broutin, I. Cerna, M. Campaniello, F. Leroux, F. Colobert, Org. Lett. 2004, 6, 4419;
33. e) M. Murata, T. Sambommatsu, S. Watanabe, Y. Masuda, Synlett 2006, 1867.
34. For a theoretical study, see: M. Sumimoto, N. Iwane, T. Takahama, S. Sakaki, J. Am. Chem. Soc. 2004, 126,10457.
35. More recently, a Cu-catalyzed borylation process was reported, see: C. Kleeberg, L. Dang, Z. Lin, T. B. Marder, Angew. Chem. 2009, 121, 5454;
36. Angew. Chem. Int. Ed. 2009, 48, 5350.
37. For reviews, see: a) T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2003, 680, 3;
38. b) I. A.I. Mkhalid, J. H. Barnard, T.B. Marder, J.C. Murphy, J.F. Hartwig, Chem. Rev. 2010, DOI: 10.1021/cr900206p.
39. For selected examples, see: a) J. Y. Cho, C.N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 2000, 122, 12868;
40. b) S. Shimada, A. S. Batsanov, J. A. K. Howard, T. B. Marder, Angew. Chem. 2001, 113, 2226;
41. Angew. Chem. Int. Ed. 2001, 40, 2168;
42. c) J. Y. Cho, M. K. Tse, M. R. Smith III, Org. Lett. 2001, 3, 2831;
43. d) J. Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith III, Science 2002, 295, 305;
44. e) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama, N. Miyaura, Tetrahedron Lett. 2002, 43, 5649;
45. f) T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem. 2002, 114, 3182;
46. Angew. Chem. Int. Ed. 2002, 41, 3056;
47. g) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390;
48. h) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig, N. Miyaura, Adv. Synth. Catal. 2003, 345, 1103;
49. i) T. Tagata, M. Nishida, Adv. Synth. Catal. 2004, 346,1655;
50. j) K. Mertins, A. Zapf, M. Beller, J. Mol. Catal. A 2004,207, 21;
51. k) T. M. Boller, J. M. Murphy, M. Hapke, T. Ishiyama, N. Miyaura, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 14263;
52. I) G. D. Frey, C.F. Rentzsch, D. V. Preysing, T. Scherg, M. Mühlhofer, E. Herdtweck, W. A. Herrmann, J. Organomet. Chem. 2006, 691, 5725;
53. m) I. A. I. Mkhalid, D. N. Coventry, D. Albesa-Jové, A. S. Batsanov, J. A. K. Howard, R. N. Perutz, T. B. Marder, Angew. Chem. 2006, 118, 503;
54. Angew. Chem. Int. Ed. 2006, 45, 489;
55. n) Y. H. Zhu, K. C Yan, J. H. Luo, C.S. Hwei, Y. C Hon, A. Emi, Z. S. Su, M. Winata, N. S. Hosmane, J. A. Maguire, J. Organomet. Chem. 2007, 692, 4244;
56. o) A. D. Finke, J. S. Moore, Org. Lett. 2008, 10, 4851;
57. p) T. A. Boebel, J. F. Hartwig, Tetrahedron 2008, 64, 6824;
58. q) T. A. Boebel, J. F. Hartwig, Organometallics 2008, 27, 6013;
59. r) T. Kikuchi, Y. Nobuta, J. Umeda, Y. Yamamoto, T. Ishiyama, N. Miyaura, Tetrahedron 2008, 64, 4967;
60. s) T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 7534;
61. t) T. Tagata, M. Nishida, A. Nishida, Tetrahedron Lett. 2009, 50, 6176;
62. u) P. Harrison, J. Morris, P. G. Steel, T. B. Marder, Synlett 2009, 147;
63. P. Harrison, J. Morris, T. B. Marder, P. G. Steel, Org. Lett. 2009, 11, 3586;
64. w) N. Iwadate, M. Suginome, J. Organomet. Chem. 2009, 694, 1713;
65. T. S. Jo, S. H. Kim, J. Shin, C. Bae, J. Am. Chem. Soc. 2009, 131,1656;
66. y) S. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura, J. Am. Chem. Soc. 2009, 131, 5058.
67. For reviews on the Sandmeyer reaction, see; a) H. H. Hodgson, Chem. Rev. 1947, 40, 251;
68. b) C. Galli, Chem. Rev. 1988, 88, 765;
69. c) E. B. Merkushev, Synthesis 1988, 923;
70. d) R. Bohlmann in Comp. Org Synth., Vol.6 (Eds.: B.M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 203.
71. For examples, see: a) D. A. Evans, J. L. Katz, G. S. Peterson, T. Hintermann, J. Am. Chem. Soc. 2001, 123,12411;
72. b) C Vergne, M. Bois-Choussy, J. Zhu, Synlett 1998, 1159.
73. For an example, see: C. Dugave, J. Org. Chem. 1995, 60, 601.
74. For an example, see: T. Cohen, A. G. Dietz, Jr., J. R. Miser, J. Org. Chem. 1977, 42, 2053.
75. H. T. Clarke, R. R. Read, Org. Synth. 1941, Vol I, 514.
76. P. A. S. Smith, B. B. Brown, J. Am. Chem. Soc. 1951, 73, 2438.
77. a) M. P. Doyle, B. Siegfried, J. F. Dellaria, Jr., J. Org. Chem. 1977, 42, 2426;
78. b) M.P. Doyle, J.F. Dellaria, Jr., B. Siegfried, S. W. Bishop, J. Org. Chem. 1977, 42, 3494.
79. J. K. Kochi, J. Am. Chem. Soc. 1957, 79, 2942.
80. See the Supporting Information for details.
81. B. Giese, Radical in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, New York, 1986.
82. C Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415.
83. J. K. Kochi, Free Radicals in Reactive Intermediate in Organic Chemistry, Vol.I, Wiley, New York, 1968, pp. 547-589.
84. For a rare example of intramolecular homolytic substitution at boron by a carbon-centered radical, see: R. A. Batey, D. V. Smil, Angew. Chem. 1999, 111, 1914;
85. Angew. Chem. Int. Ed. 1999, 38, 1798.