Pinacolborane as the boron source in nitrogen-directed borylations of aromatic N, N -dimethylhydrazones

Journal of Organic Chemistry

Volumn 77, Issue 21, 2012, Pages 9915-9920

  López Rodríguez, Rocío ^a,b   Ros, Abel ^a   Fernández, Rosario ^b   Lassaletta, José M ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZONITRILES; BORYLATION; CROSS-COUPLINGS; FUNCTIONALIZED; HIGH REACTIVITY; N ,N-LIGAND; ONE POT; PINACOLBORANE; SUZUKI-MIYAURA;

BORON; IRIDIUM;

AROMATIC COMPOUNDS;

4 AMINOPYRIDINE DERIVATIVE; 4 N,N DIMETHYLAMINOPYRIDINE; BENZONITRILE; BORANE DERIVATIVE; HYDRAZONE DERIVATIVE; N,N DIMETHYLHYDRAZONE; NITROGEN; PINACOLBORANE; SARTAN DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BORYLATION; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CROSS REACTION; METHODOLOGY; ONE POT SYNTHESIS; SUZUKI REACTION;

BORON; BORON COMPOUNDS; CATALYSIS; HYDRAZONES; IRIDIUM; METHYLAMINES; MOLECULAR STRUCTURE; NITRILES; NITROGEN; PYRIDINES;

EID: 84868351314     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301965v     Document Type: Article

References (35)

1. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988.
2. Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005.
3. Cho, J. Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868
4. Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305
5. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390
6. Review: Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
7. Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. Chem. Commun. 2003, 2924
8. Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka, R. E., Jr.; Smith, M. R., III. J. Am. Chem. Soc. 2006, 128, 15552
9. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168
10. Boebel, A.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534
11. Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131, 5058
12. Kawamorita, S.; Ohmiya, H.; Sawamura, M. J. Org. Chem. 2010, 75, 3855
13. Yamazaki, K.; Kawamorita, S.; Ohmiya, H.; Sawamura, M. Org. Lett. 2010, 12, 3978
14. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
15. Ishiyama, T.; Isou, H.; Kikuchi, T.; Miyaura, N. Chem. Commun. 2010, 46, 159
16. Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068
17. Roosen, P. C.; Kallepalli, V. A.; Chattopadhyay, B.; Singleton, D. A.; Maleczka, R. E., Jr.; Smith, M. R., III. J. Am. Chem. Soc. 2012, 134, 11350
18. Kawamorita, S.; Miyazaki, T.; Ohmiya, H.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2011, 133, 19310
19. Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 134
20. Xiao, B.; Li, Y.-M.; Liu, Z.-J.; Yang, H.-Y.; Fu, Y. Chem. Commun. 2012, 48, 4854
21. Ros, A.; Estepa, B.; López-Rodríguez, R.; álvarez, E.; Fernández, R.; Lassaletta, J. M. Angew. Chem., Int. Ed. 2011, 50, 11724
22. Ros, A.; López-Rodríguez, R.; Estepa, B.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2012, 134, 4573
23. The effect of introduction of donating- and electron-withdrawing groups in ligands for nondirected borylation has been studied. See: Ishiyama, T.; Takagi, J.; Hartwig, J. F; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056
24. Gros, P.; Fort, Y.; Caubére, P. J. Chem. Soc., Perkin Trans. 1 1997, 3597
25. Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238
26. Wexler, R. R.; Greenlee, W. J.; Irvin, J. D.; Goldberg, M. R.; Prendergast, K.; Smith, R. D.; Timmermans, P. B. M. W. M. J. Med. Chem. 1996, 39, 625
27. Blakeney, J. S.; Reid, R. C.; Le, G. T.; Fairlie, D. P. Chem. Rev. 2007, 107, 2960
28. Naik, P.; Murumkar, P.; Giridhar, R.; Yadav, M. R. Bioorg. Med. Chem. 2010, 18, 8418 and references cited therein
29. Hydrazone to nitrile tranformation was carried out following a known procedure: Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M.; Vázquez, J. Tetrahedron Lett. 1993, 34, 141
30. Bromination reaction was carried out following: Huszar, C.; árvai, G.; Hegedus, A. WO/2011/073703.
31. Barret, I. C.; Langille, J. D.; Kerr, M. A. J. Org. Chem. 2000, 65, 6268
32. Petroski, R. J. Synth. Commun. 2006, 12, 1727
33. Hwu, J. R.; Wang, N. Tetrahedron 1988, 44, 4181
34. Goossen, L. J.; Melzer, B. J. Org. Chem. 2007, 72, 7473
35. Kristensen, J.; Lysén, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435