Ir-catalyzed borylation of C-H bonds in N-containing heterocycles: Regioselectivity in the synthesis of heteroaryl boronate esters

Angewandte Chemie - International Edition

Volumn 45, Issue 3, 2006, Pages 489-491

  Mkhalid, Ibraheem A I ^a   Coventry, David N ^a   Albesa Jove, David ^a   Batsanov, Andrei S ^a   Howard, Judith A K ^a   Perutz, Robin N ^b   Marder, Todd B ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Boron; Boronate esters; Boronic acid heterocycles; C H activation; Structure elucidation

Indexed keywords

ACTIVATION ENERGY; BORON; CATALYSIS; ESTERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BORONATE ESTERS; BORONIC ACID HETEROCYCLES; C-H ACTIVATION; STRUCTURE ELUCIDATION;

IRIDIUM;

EID: 30444451469     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503047     Document Type: Article

References (32)

1. a) A. Suzuki, N. Miyaura, Chem. Rev. 1995, 95, 2451;
2. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147;
3. c) P. R. Parry, C. Wang, A. S. Batsanov, M. R. Bryce, B. Tarbit, J. Org. Chem. 2002, 67, 7541;
4. d) F. Türksoy, G. Hughes, A. S. Batsanov, M. R. Bryce, J. Mater. Chem. 2003, 13, 1554;
5. e) P. R. Parry, M. R. Bryce, B. Tarbit, Synthesis 2003, 1035;
6. f) N. Saygili, A. S. Batsanov, M. R. Bryce, Org. Biomol. Chem. 2004, 2, 852;
7. g) A. E. Thompson, G. Hughes, A. S. Batsanov, M. R. Bryce, P. R. Parry, B. Tarbit, J. Org. Chem. 2005, 70, 388.
8. D. M. T. Chan, K. L. Monaco, R. Li, D. Bonne, C. G. Clark, P. Y. S. Lam, Tetrahedron Lett. 2003, 44, 3863.
9. a) M. P. Sibi, H. Tatamidani, K. Patil, Org. Lett. 2005, 7, 2571;
10. b) G. Chen, N. Tokunaga, T. Hayashi, Org. Lett. 2005, 7, 2885.
11. a) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. Hartwig, J. Am. Chem. Soc. 2002, 124, 390;
12. b) T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem. 2002, 114, 3182;
13. Angew. Chem. Int. Ed. 2002, 41, 3056.
14. J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr., M. R. Smith III, Science 2002, 295, 305.
15. P. Nguyen, H. P. Blom, S. A. Westcott, N. J. Taylor, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 9329.
16. H. Tamura, H. Yamazaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 2003, 125, 16114.
17. D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder, R. N. Perutz, Chemm. Commun. 2005, 2172.
18. J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama, N. Miyaura, Tetrahedron Lett. 2002, 43, 5649.
19. T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2003, 680, 3.
20. a) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig, N. Miyaura, Adv. Synth. Catal. 2003, 345, 1103;
21. b) T. Ishiyama, Y. Nobuta, J. F. Hartwig, N. Miyaura, Chem. Commun. 2003, 2942.
22. a) J.-Y. Cho, C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 2000, 122, 12868;
23. b) T. Tagata, M. Nishida, Adv. Synth. Catal. 2004, 346, 1655.
24. G. A. Chotana, M. A. Rak, M. R. Smith, III, J. Am. Chem. Soc. 2005, 127, 10539.
25. -3. CCDC 279973-279978 contain the supplementary crystallographic 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.
26. a) M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett. 2005, 75, 4;
27. b) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzag, H. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304;
28. c) C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys. 2001, 90, 5048.
29. The only reference to this compound we have located is in the following patent: Jpn. Kokai Tokkyo Koho, 1980, 6 pp, CODEN: JKXXAF JP 55120570 19800917 Showa. [Chem. Abstr. 1981, 94, 175164].
30. a) T. B. Hadda, I. Zidane, S. A. Moya, H. Le Bozec, Polyhedron 1996, 15, 1571;
31. b) M. Lepeltier, T. K.-M. Lee, K. K.-W. Lo, L. Toupet, H. Le Bozec, V. Guerchais, Eur. J. Inorg. Chem. 2005, 110;
32. c) W. Lu, B.-X. Mi, M. C. W. Chan, Z. Hui, C.-M. Che, N. Zhu, S.-T. Lee, J. Am. Chem. Soc. 2004, 126, 4958.