Catalytic functionalization of methyl group on silicon: Iridium-catalyzed C(sp3)-H borylation of methylchlorosilanes

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17416-17419

  Ohmura, Toshimichi ^a   Torigoe, Takeru ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORYLATION; CATALYTIC FUNCTIONALIZATION; CHLOROSILANES; METHYL GROUP;

CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; IRIDIUM;

CATALYSIS;

BORON; CARBON; CYCLOHEXANE; HYDROGEN; IRIDIUM; METHYL GROUP; METHYLCHLOROSILANE DERIVATIVE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; ATOM; BORYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HYDROGEN BOND; SUBSTITUTION REACTION; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; IRIDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SILANES; SILICON;

EID: 84867763107     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307956w     Document Type: Article

References (51)

1. Rochow, E. G. J. Am. Chem. Soc. 1945, 67, 963
2. Rochow, E. G. Silicon and Silicones; Springer-Verlag: 1987.
3. Rappoport, Z.; Apeloig, Y., Eds. The Chemistry of Organosilicon Compounds, Vol. 2; Wiley: 1998.
4. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley-Interscience: 2000.
5. Beckmann, J. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, M. P., Eds.; Elsevier: 2007; Vol. 3, p 409.
6. Fuchs, P. L., Ed. Reagents for Silicon-Mediated Organic Synthesis; Wiley: 2011.
7. Krieble, R. H.; Elliott, J. R. J. Am. Chem. Soc. 1945, 67, 1810
8. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
9. Stowers, K. J.; Fortner, K. C.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 6541
10. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
11. Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070
12. Young, A. J.; White, M. C. Angew. Chem., Int. Ed. 2011, 50, 6824
13. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
14. Ihara, H.; Ueda, A.; Suginome, M. Chem. Lett. 2011, 40, 916
15. Novák, P.; Correa, A.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2011, 50, 12236
16. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
17. Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763
18. Simmons, E. M.; Hartwig, J. F. Nature 2012, 483, 70
19. Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313
20. Xie, P.; Xie, Y.; Qian, B.; Zhou, H.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 9902
21. Manabe, T.; Yanagi, S.; Ohe, K.; Uemura, S. Organometallics 1998, 17, 2942
22. Liang, Y.; Geng, W.; Wei, J.; Ouyang, K.; Xi, Z. Org. Biomol. Chem. 2012, 10, 1537
23. Iverson, C. N.; Smith, M. R., III J. Am. Chem. Soc. 1999, 121, 7696
24. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305
25. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390
26. Ishiyama, T; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056
27. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
28. Ishiyama, T.; Miyaura, N. In Boronic Acids, 2nd ed.; Hall, D., Ed.; Wiley-VCH: 2011; Vol. 1, p 135.
29. Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38, 3391
30. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995
31. Kondo, Y.; García-Cuadrado, D.; Hartwig, J. F.; Boaen, N. K.; Wagner, N. L.; Hillmyer, M. A. J. Am. Chem. Soc. 2002, 124, 1164
32. Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 15334
33. Bae, C.; Hartwig, J. F.; Harris, N. K. B.; Long, R. O.; Anderson, K. S.; Hillmyer, M. A. J. Am. Chem. Soc. 2005, 127, 767
34. Bae, C.; Hartwig, J. F.; Chung, H.; Harris, N. K.; Switek, K. A.; Hillmyer, M. A. Angew. Chem., Int. Ed. 2005, 44, 6410
35. Murphy, J. M.; Lawrence, J. D.; Kawamura, K.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 13684
36. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168
37. Ishiyama, T.; Ishida, K.; Takagi, J.; Miyaura, N. Chem. Lett. 2001, 30, 1082
38. Boebel, T. A.; Hartwig, J. F. Organometallics 2008, 27, 6013
39. Olsson, V. J.; Szabó, K. J. Angew. Chem., Int. Ed. 2007, 46, 6891
40. Caballero, A.; Sabo-Etienne, S. Organometallics 2007, 26, 1191
41. Olsson, V. J.; Szabó, K. J. J. Org. Chem. 2009, 74, 7715
42. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 12422
43. Kawamorita, S.; Miyazaki, T.; Iwai, T; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 12924
44. The directing effect of a chlorine atom has been observed in the ortho -selective C-H borylation of chlorobenzenes using a silica-supported phosphine-iridium catalyst. Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131, 5058
45. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114
46. Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263
47. 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
48. Jiang, H.; Zhu, S. Tetrahedron Lett. 2005, 46, 517
49. Sadhu, K. M.; Matteson, D. S. Organometallics 1985, 4, 1687
50. Tamao, K.; Nakagawa, Y.; Ito, Y. Org. Synth. 1996, 73, 94
51. Bennetau, B.; Dunogues, J. Tetrahedron Lett. 1983, 24, 4217