High-throughput optimization of Ir-catalyzed C-H borylation: A tutorial for practical applications

Journal of the American Chemical Society

Volumn 135, Issue 20, 2013, Pages 7572-7582

  Preshlock, Sean M ^a   Ghaffari, Behnaz ^a   Maligres, Peter E ^b   Krska, Shane W ^b   Maleczka, Robert E ^a   Smith, Milton R ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON REAGENTS; BORYLATION; CATALYTIC CONDITIONS; HIGH-THROUGHPUT; HIGH-THROUGHPUT SCREENING; PRECATALYSTS; REACTION CONDITIONS;

IRIDIUM; SUBSTRATES;

CATALYSIS;

BORON; CARBON; HYDROGEN; IRIDIUM;

ARTICLE; BORYLATION; CATALYSIS; CHEMICAL REACTION;

BORON COMPOUNDS; CATALYSIS; HIGH-THROUGHPUT SCREENING ASSAYS; IRIDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84878226561     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja400295v     Document Type: Article

References (59)

1. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
2. Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305
3. Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263
4. 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
5. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114
6. Chotana, G. A.; Vanchura, B. A., II; Tse, M. K.; Staples, R. J.; Maleczka, R. E., Jr.; Smith, M. R., III Chem. Commun. 2009, 5731
7. Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056
8. The following articles on C-H borylation have been published since the review article cited in ref 1: Kallepalli, V. A.; Sanchez, L.; Li, H.; Gesmundo, N. J.; Turton, C. L.; Maleczka, R. E., Jr.; Smith, M. R., III Heterocycles 2010, 80, 1429
9. Liskey, C. W.; Liao, X. B.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389
10. Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068
11. Yamazaki, K.; Kawamorita, S.; Ohmiya, H.; Sawamura, M. Org. Lett. 2010, 12, 3978
12. Itoh, H.; Kikuchi, T.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2011, 40, 1007
13. Li, G. Q.; Kiyomura, S.; Yamamoto, Y.; Miyaura, N. Chem. Lett. 2011, 40, 702
14. Liao, X. B.; Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2088
15. Nguyen, D. H.; Perez-Torrente, J. J.; Lomba, L.; Jimenez, M. V.; Lahoz, F. J.; Oro, L. A. Dalton Trans. 2011, 40, 8429
16. Norberg, A. M.; Smith, M. R., III; Maleczka, R. E., Jr. Synthesis 2011, 857
17. Ozawa, R.; Yoza, K.; Kobayashi, K. Chem. Lett. 2011, 40, 941
18. Ros, A.; Estepa, B.; Lopez-Rodriguez, R.; Alvarez, E.; Fernandez, R.; Lassaletta, J. M. Angew. Chem., Int. Ed. 2011, 50, 11724
19. Teraoka, T.; Hiroto, S.; Shinokubo, H. Org. Lett. 2011, 13, 2532
20. Cheng, J. H.; Yi, C. L.; Liu, T. J.; Lee, C. F. Chem. Commun. 2012, 48, 8440
21. Crawford, A. G.; Liu, Z. Q.; Mkhalid, I. A. I.; Thibault, M. H.; Schwarz, N.; Alcaraz, G.; Steffen, A.; Collings, J. C.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Chem.-Eur. J. 2012, 18, 5022
22. Eliseeva, M. N.; Scott, L. T. J. Am. Chem. Soc. 2012, 134, 15169
23. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864
24. Hitosugi, S.; Nakamura, Y.; Matsuno, T.; Nakanishi, W.; Isobe, H. Tetrahedron Lett. 2012, 53, 1180
25. Hume, P.; Furkert, D. P.; Brimble, M. A. Tetrahedron Lett. 2012, 53, 3771
26. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 12422
27. Liu, T. F.; Shao, X. X.; Wu, Y. M.; Shen, Q. L. Angew. Chem., Int. Ed. 2012, 51, 540
28. Ohmura, T.; Torigoe, T.; Suginome, M. J. Am. Chem. Soc. 2012, 134, 17416
29. Robbins, D. W.; Hartwig, J. F. Org. Lett. 2012, 14, 4266
30. Roering, A. J.; Hale, L. V. A.; Squier, P. A.; Ringgold, M. A.; Wiederspan, E. R.; Clark, T. B. Org. Lett. 2012, 14, 3558
31. 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
32. Ros, A.; Lopez-Rodriguez, R.; Estepa, B.; Alvarez, E.; Fernandez, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2012, 134, 4573
33. Wang, C.; Sperry, J. J. Org. Chem. 2012, 77, 2584
34. Bruck, A.; Gallego, D.; Wang, W. Y.; Irran, E.; Driess, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 11478
35. Partridge, B. M.; Hartwig, J. F. Org. Lett. 2012, 15, 140
36. López-Rodríguez, R.; Ros, A.; Fernández, R.; Lassaletta, J. M. J. Org. Chem. 2012, 77, 9915
37. Robbins, D. W.; Hartwig, J. F. Angew. Chem., Int. Ed. 2013, 933
38. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 3375
39. Lee, C.-I.; Zhou, J.; Ozerov, O. V. J. Am. Chem. Soc. 2013, 135, 3560
40. Kawamorita, S.; Murakami, R.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2013, 135, 2947
41. Chang, Y.; Lee, H. H.; Kim, S. H.; Jo, T. S.; Bae, C. Macromolecules 2013, 46, 1754
42. Tajuddin, H.; Harrisson, P.; Bitterlich, B.; Collings, J. C.; Sim, N.; Batsanov, A. S.; Cheung, M. S.; Kawamorita, S.; Maxwell, A. C.; Shukla, L.; Morris, J.; Lin, Z.; Marder, T. B.; Steel, P. G. Chem. Sci. 2012, 3, 3505
43. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257
44. Shultz, C. S.; Krska, S. W. Acc. Chem. Res. 2007, 40, 1320
45. Abboud, J. L. M.; Notario, R. Pure Appl. Chem. 1999, 71, 645
46. +: Mestroni, G.; Camus, A.; Zassinovich, G. J. Organomet. Chem. 1974, 73, 119
47. Filipuzzi, S.; Farnetti, E. J. Mol. Catal. A: Chem. 2005, 238, 111
48. Vanchura, B. A., II, Ph.D. Thesis, Michigan State University: East Lansing, MI, 2010.
49. Connor, J. A.; Overton, C. J. Organomet. Chem. 1983, 249, 165
50. Leidner, C. R.; Murray, R. W. J. Am. Chem. Soc. 1984, 106, 1606
51. Nazeeruddin, M. K.; Zakeeruddin, S. M.; Kalyanasundaram, K. J. Phys. Chem. 1993, 97, 9607
52. Johnson, R.; Madhani, H.; Bullock, J. P. Inorg. Chim. Acta 2007, 360, 3414
53. Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 6686
54. Hazell, A. C.; Hazell, R. G. Acta Crystallogr., Sect.C: Cryst. Struct. Commun. 1984, 40, 806
55. Andersen, P.; Josephsen, J. Acta Chem. Scand. 1971, 25, 3255
56. Yoshikawa, N.; Sakamoto, J.; Kanehisa, N.; Kai, Y.; Matsumura-Inoue, T. Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, 59, m155
57. Dervisi, A.; Carcedo, C.; Ooi, L. Adv. Synth. Catal. 2006, 348, 175
58. Upadhayaya, R. S.; Shinde, P. D.; Sayyed, A. Y.; Kadam, S. A.; Bawane, A. N.; Poddar, A.; Plashkevych, O.; Foeldesi, A.; Chattopadhyaya, J. Org. Biomol. Chem. 2010, 8, 5661
59. Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Eur. J. Med. Chem. 2004, 39, 249