Synthesis of pinacol arylboronates from aromatic amines: A metal-free transformation

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 1923-1933

  Qiu, Di ^a   Jin, Liang ^a   Zheng, Zhitong ^a   Meng, He ^a   Mo, Fanyang ^a   Wang, Xi ^a   Zhang, Yan ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS;

AROMATIC AMINES; ARYLBORONATES; FUNCTIONALIZED; PROCESS-BASED; RADICAL SPECIES; REACTION CONDITIONS; REACTION MECHANISM; SUZUKI-MIYAURA CROSS-COUPLING;

AMINES;

ANILINE DERIVATIVE; AROMATIC AMINE; BORON DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DECOMPOSITION; ELECTRON TRANSPORT; HIGH TEMPERATURE; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 84874074837     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3018878     Document Type: Article

References (91)

1. Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2 nd ed.; Wiley-VCH: Weinheim, 2011.
2. Suzuki, A. Acc. Chem. Res. 1982, 15, 178
3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
4. Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 49-97.
5. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
6. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633
7. Miyaura, N. J. Organomet. Chem. 2002, 653, 54
8. Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271
9. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
10. Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565
11. Wang, C.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 5240
12. Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2010, 49, 7164
13. Brown, H. C.; Srebnik, M.; Cole, T. E. Organometallics 1986, 5, 2300
14. Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316
15. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508
16. Ishiyama, T.; Miyaura, N. J. Synth. Org. Chem. Jpn. 1999, 57, 503
17. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392
18. Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458
19. Murata, M.; Oyama, T.; Watanbe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164
20. Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268
21. Broutin, P.; Cerna, I.; Campaniello, M.; Leroux, F.; Colobert, F. Org. Lett. 2004, 6, 4419
22. Murata, M.; Sambommatsu, T.; Watanabe, S.; Masuda, Y. Synlett 2006, 1867
23. Zhu, W.; Ma, D. Org. Lett. 2006, 8, 261
24. Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350
25. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3
26. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. C.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
27. Ingleson, M. J. Synlett 2012, 23, 1411
28. De Vries, T. S.; Prokofjevs, A.; Vedejs, E. Chem. Rev. 2012, 112, 4246
29. Ishida, N.; Moriya, T.; Goya, T.; Murakami, M. J. Org. Chem. 2010, 75, 8709
30. Del Grosso, A.; Muryn, C. A.; Pritchard, R. G.; Ingleson, M. J. Organometallics 2010, 29, 241
31. Del Grosso, A.; Singleton, P. J.; Muryn, C. A.; Ingleson, M. J. Angew. Chem., Int. Ed. 2011, 50, 2102
32. Prokofjevs, A.; Kampf, J. W.; Vedejs, E. Angew. Chem., Int. Ed. 2011, 50, 2098
33. Del Grosso, A.; Helm, M. D.; Solomon, S. A.; Caras-Quintero, D.; Ingleson, M. J. Chem. Commun. 2011, 47, 12459
34. Solomon, S. A.; Del, Grosso, A.; Clark, E. R.; Bagutski, V.; McDouall, J. J. W.; Ingleson, M. J. Organometallics 2012, 31, 1908
35. Niu, L.; Yang, H.; Yang, D.; Fua, H. Adv. Synth. Catal. 2012, 354, 2211-2217
36. Mo, F.; Jiang, Y.; Qiu, D.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2010, 49, 1846
37. Doyle, M. P.; Siegfried, B.; Dellaria, J. F., Jr. J. Org. Chem. 1977, 42, 2426
38. Doyle, M. P.; Dellaria, J. F., Jr.; Siegfried, B.; Bishop, S. W. J. Org. Chem. 1977, 42, 3494
39. Hodgson, H. H. Chem. Rev. 1947, 40, 251
40. Galli, C. Chem. Rev. 1988, 88, 765
41. Merkushev, E. B. Synthesis 1988, 923
42. Bohlmann, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon, Oxford, 1991; 6, 203.
43. Balz, G.; Schiemann, G. Ber. 1927, 60B, 1186
44. While this manuscript was under preparation, Yamane et. al reported a deaminoborylation of aryltriazene with bis(pinacolato)diboron, see: Zhu, C.; Yamane, M. Org. Lett. 2012, 14, 4560
45. Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942
46. Giese, B. Radical in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: New York, 1986.
47. Claudel, S.; Gosmini, C.; Paris, J. M.; Périchon, J. Chem. Commun. 2007, 3667
48. Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359
49. Lu, J.; Guan, Z.; Gao, J.; Zhang, Z. Appl. Organometal. Chem. 2011, 25, 537
50. Kumar, A.; Ye, G.; Ahmadibeni, Y.; Parang, K. J. Org. Chem. 2006, 71, 7915
51. Harvey, J. H.; Butler, B. K.; Trauner, D. Tetrahedron Lett. 2007, 48, 1661
52. Cambre, J. N.; Roy, D.; Gondi, S. R.; Sumerlin, B. S. J. Am. Chem. Soc. 2007, 129, 10348
53. Lei, S.; Ver Heyen, A.; De Feyter, S.; Surin, M.; Lazzaroni, R.; Rosenfeldt, S.; Ballauff, M.; Lindner, P.; Mössinger, D.; Höger, S. Chem.-Eur. J. 2009, 15, 2518
54. Lipshutz, B. H.; Moser, R.; Voigtritter, K. R. Isr. J. Chem. 2010, 50, 691
55. O'Connella, D. P.; LeBlanca, D. F.; Cromleyb, D.; Billheimerb, J.; Raderb, D. J.; Bachovchin, W. W. Bioorg. Med. Chem. Lett. 2012, 22, 1397
56. Gross, J. L.; Williams, M. J.; Stack, G. P.; Gao, H.; Zhou, D. PCT Int. Appl. 2005, 2005044812.
57. Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131, 5058
58. Billingsley, K. L.; Buchwald, S. L. J. Org. Chem. 2008, 73, 5589
59. Gonzalez-Rodriguez, D.; Carbonell, E.; Guldi, D. M.; Torres, T. Angew. Chem., Int. Ed. 2009, 48, 8032
60. Kianmehr, E.; Yahyaee, M.; Tabatabai, K. Tetrahedron 2007, 48, 2713
61. Rentzsch, C. F.; Tosh, E.; Herrmann, W. A.; Kuehn, F. E. Green Chem. 2009, 11, 1610
62. Qiu, D.; Mo, F.; Zheng, Z.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 5474
63. Cho, J.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305
64. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390
65. Chotana, G. A.; Rak, M. A.; Smith, M. R., III. J. Am. Chem. Soc. 2005, 127, 10539
66. Dunach, I.; Olivero, S.; Pintaric, C. PCT Int. Appl. 2010, 2010055245.
67. Vanchura, B. A., II; Preshlock, S. M.; Roosen, P. C.; Kallepalli, V. A.; Staples, R. J.; Maleczka, R. E., Jr.; Singleton, D. A.; Smith, M. R., III. Chem. Commun. 2010, 46, 7724
68. Tang, W.; Keshipeddy, S.; Zhang, Y.; Wei, X.; Savoie, J.; Patel, N. D.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2011, 13, 1366
69. Aspinall, M. B.; Mound, W. R.; Wailes, J. S.; Whittingham, W. G.; Williams, J.; Winn, C. L.; Worthington, P. A. PCT Int. Appl. 2009, 2009081112.
70. Doux, M.; Mézailles, N.; Melaimi, M.; Ricard, L.; Le Floch, P. Chem. Commun. 2002, 1566
71. Moon, T. C.; Quan, Z.; Kim, J.; Kim, H. P.; Kudo, I.; Murakami, M.; Park, H.; Chang, H. W. Bioorg. Med. Chem. 2007, 15, 7138
72. Appukkuttan, P.; Van der Eycken, E.; Dehaen, W. Synlett 2003, 1204
73. Ouk, S.; Vernier, J.; Gunic, E.; Chen, C. PCT Int. Appl. 2011, 2011159839.
74. Sośnicki, J. K. Synlett 2009, 2508
75. Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren, S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 6352
76. Fan, X.; Yang, L. Eur. J. Org. Chem. 2010, 2457
77. Yamada, Y. M. A.; Sarkar, S. M.; Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 3190
78. an der Heiden, M.; Plenio, H. Chem.-Eur. J. 2004, 10, 1789
79. Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zecri, F. J. Org. Lett. 1999, 1, 579
80. Fitzmaurice, R. J.; Etheridge, Z. C.; Jumel, E.; Woolfson, D. N.; Caddick, S. Chem. Commun. 2006, 4814
81. Wang, L.; Cui, X.; Li, J.; Wu, Y.; Zhu, Z.; Wu, Y. Eur. J. Org. Chem. 2012, 595
82. Ye, M.; Gao, G.; Edmunds, A. J. F.; Worthington, P. A.; Morris, J. A.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19090
83. Thompson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49, 5237
84. Louaisil, N.; Pham, P. D.; Boeda, F.; Faye, D.; Castanet, A.; Legoupy, S. Eur. J. Org. Chem. 2011, 143
85. Liu, C.; Han, N.; Song, X.; Qiu, J. Eur. J. Org. Chem. 2010, 5548
86. Zhang, J.; Wu, Y.; Zhu, Z.; Ren, G.; Mak, T. C. W.; Song, M. Appl. Organometal. Chem. 2007, 21, 935
87. Corte, J.; Hangeland, J.; Quan, M.; Smallheer, J. M.; Fang, T. PCT Int. Appl. 2005, 2005123680.
88. El Hankari, S.; El Kadib, A.; Finiels, A.; Bouhaouss, A.; Moreau, J. J. E.; Crudden, C. M.; Brunel, D.; Hesemann, P. Chem.-Eur. J. 2011, 17, 8984
89. Xu, L.; Li, B.; Wu, Z.; Lu, X.; Guan, B.; Wang, B.; Zhao, K.; Shi, Z. Org. Lett. 2010, 12, 884
90. Wolf, C.; Ekoue-Kovi, K. Eur. J. Org. Chem. 2006, 1917
91. Li, P.; Zhao, J.; Wu, C.; Larock, R. C.; Shi, F. Org. Lett. 2011, 13, 3340