Suzuki-Miyaura cross-coupling reactions of potassium boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3138-3141

  Molander, Gary A ^a   Shin, Inji ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; FLUORINE DERIVATIVE; MESYLIC ACID DERIVATIVE; POTASSIUM;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; OXIDATION REDUCTION REACTION;

AMINATION; BORIC ACIDS; FLUORINE COMPOUNDS; MESYLATES; METHYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POTASSIUM;

EID: 84862520482     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301221p     Document Type: Article

References (40)

1. Musher, D. M.; Fainstein, V.; Young, E. J. Antimicrob. Agents Chemother. 1980, 254
2. Campoli-Richards, D.; Lackner, T.; Monk, J. Drug 1987, 34, 411
3. Kaczanowska, K.; Wiesmüller, K.-H.; Schaffner, A.-P. ACS Med. Chem. Lett. 2010, 1, 530
4. Nystrom, R. F.; Brown, W. G. J. Am. Chem. Soc. 1948, 70, 3738
5. Soffer, L. M.; Katz, M. J. Am. Chem. Soc. 1956, 78, 1705
6. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5448
7. Bair, K. W.; Tuttle, R. L.; Knick, V. C.; Cory, M.; McKee, D. D. J. Med. Chem. 1990, 33, 2385
8. Knölker, H.-J.; Filali, S. Synlett 2003, 11, 1752
9. Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437
10. Gololobov, Y. G.; Kaukhin, L. F. Tetrahedron 1992, 48, 1353
11. Agrawal, J. P.; Hodgson, R. Organic Chemistry of Explosives; Wiley: Chichester, 2007.
12. Huynh, M.-H. V.; Hiskey, M. A.; Chavez, D. E.; Naud, D. L.; Gilardi, R. D. J. Am. Chem. Soc. 2005, 127, 12537
13. Molander, G. A.; Fleury-Brégeot, N.; Hiebel, M.-A. Org. Lett. 2011, 13, 1694
14. Tanaka, K. PCT Int. Appl. WO 2008007670, 2008.
15. Devulapally, R.; Fleury-Brégeot, N.; Molander, G. A.; Seapy, D. G. Tetrahedron Lett. 2012, 53, 1051
16. Molander, G. A.; Shin, I. Org. Lett. 2011, 13, 3956
17. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3 rd ed.; John Wiley & Sons: New York, 1999.
18. Kocienski, P. J. Protecting Groups, 3 rd ed.; Georg Thieme: Stuttgart, NY, 2005.
19. Hasan, I.; Marinelli, E. R.; Lin, L.-C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157
20. Ravinder, K.; Reddy, V.; Mahesh, K. C.; Narasimhulu, M.; Venkateswarlu, Y. Synth. Commun. 2007, 37, 281
21. du Vigneaud, V.; Behrens, O. K. J. Biol. Chem. 1937, 117, 27
22. Kharasch, M. S.; Priestley, H. M. J. Am. Chem. Soc. 1939, 61, 3425
23. Snyder, H. R.; Heckert, R. E. J. Am. Chem. Soc. 1952, 74, 2006
24. Li, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311
25. Fan, X.-H.; Yang, L.-M. Eur. J. Org. Chem. 2011, 1467
26. So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7731
27. Petersen, M. D.; Boye, S. V.; Nielsen, E. H.; Willumsen, J.; Sinning, S.; Wiborg, O.; Bols, M. Bioorg. Med. Chem. 2007, 15, 4159
28. Zhang, L. A.; Meng, T. H.; Wu, J. J. Org. Chem. 2007, 72, 9346
29. Lipshutz, B. H.; Butler, T.; Swift, E. Org. Lett. 2008, 10, 697
30. Leowanawat, P.; Zhang, N.; Resmerita, A.-M.; Rosen, B. M.; Percec, V. J. Org. Chem. 2011, 76, 9946
31. Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2010, 75, 5109
32. Molander, G. A.; Beaumard, F. Org. Lett. 2010, 12, 4022
33. Kuroda, J. I.; Inamoto, K.; Hiroya, K.; Doi, T. Eur. J. Org. Chem. 2009, 2251
34. Bhayana, B.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2009, 11, 3954
35. So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 8059
36. So, C. M.; Kwong, F. Y. Chem. Soc. Rev. 2011, 40, 4963-4972
37. Molander, G. A.; Beaumard, F. Org. Lett. 2011, 13, 3948
38. Molander, G. A.; Beaumard, F.; Niethamer, T. K. J. Org. Chem. 2011, 76, 8126
39. Molander, G. A.; Beaumard, F. Org. Lett. 2011, 13, 1242
40. Alami, M.; Amatore, C.; Bensalem, S.; Choukchou-Brahim, A.; Jutand, A. Eur. J. Inorg. Chem. 2001, 2675