Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3956-3959

  Molander, Gary A ^a   Shin, Inji ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; FLUORINE; FORMIC ACID DERIVATIVE; HALOGEN; POTASSIUM; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; METHYLATION; SYNTHESIS;

AMINATION; BORIC ACIDS; DIMERIZATION; FLUORINE; FORMIC ACID ESTERS; HALOGENS; METHYLATION; MOLECULAR STRUCTURE; POTASSIUM;

EID: 79961096949     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2014768     Document Type: Article

References (35)

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. Miller, J. F.; Gudmundsson, K. S.; Richardson, L. D.; Jenkinson, S.; Spaltenstein, A.; Thomson, M.; Wheelan, P. Bioorg. Med. Chem. Lett. 2010, 20, 3026
5. Aliabadi, A.; Shamsa, F.; Ostad, S. N.; Emami, S.; Shafiee, A.; Davoodi, J.; Foroumadi, A. Eur. J. Med. Chem. 2010, 45, 5348
6. Shukla, N. M.; Mutz, C. A.; Ukani, R.; Warshakoon, H. J.; Moore, D. S.; David, S. A. Bioorg. Med. Chem. Lett. 2010, 20, 6384
7. Liu, G.-S.; Dong, Q.-L.; Yao, Y.-S.; Yao, Z.-J. Org. Lett. 2008, 10, 5393
8. Nystrom, R. F.; Brown, W. G. J. Am. Chem. Soc. 1948, 70, 3738
9. Soffer, L. M.; Katz, M. J. Am. Chem. Soc. 1956, 78, 1705
10. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5448
11. Bair, K. W.; Tuttle, R. L.; Knick, V. C.; Cory, M.; McKee, D. D. J. Med. Chem. 1990, 33, 2385
12. Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437
13. Gololobov, Y. G.; Kaukhin, L. F. Tetrahedron 1992, 48, 1353
14. Knölker, H.-J.; Filali, S. Synlett 2003, 11, 1752
15. Agrawal, J. P.; Hodgson, R. In Organic Chemistry of Explosives; Wiley: Chichester, 2007.
16. Huynh, M.-H. V.; Hiskey, M. A.; Chavez, D. E.; Naud, D. L.; Gilardi, R. D. J. Am. Chem. Soc. 2005, 127, 12537
17. Molander, G. A.; Hiebel, M.-A. Org. Lett. 2010, 12, 4876
18. Molander, G. A.; Fleury-Brégeot, N.; Hiebel, M.-A. Org. Lett. 2011, 13, 16937
19. Molander, G. A.; Sandrock, D. L. Org. Lett. 2007, 9, 1597
20. Hasník, Z; Pohl, R.; Hocek, M. Synthesis 2009, 8, 1309
21. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3 rd ed.; John Wiley & Sons: New York, 1999.
22. Kocienski, P. J. Protecting Groups, 3 rd ed.; Georg Thieme: Stuttgart, NY, 2005.
23. Hasan, I.; Marinelli, E. R.; Lin, L.-C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157
24. Ravinder, K.; Reddy, V.; Mahesh, K. C.; Narasimhulu, M.; Venkateswarlu, Y. Synth. Commun. 2007, 37, 281
25. du Vigneaud, V.; Behrens, O. K. J. Biol. Chem. 1937, 117, 27
26. Kharasch, M. S.; Priestley, H. M. J. Am. Chem. Soc. 1939, 61, 3425
27. Snyder, H. R.; Heckert, R. E. J. Am. Chem. Soc. 1952, 74, 2006
28. Li, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311
29. Tanaka, K. PCT Int. Appl. WO 2008007670, 2008.
30. Matteson, D. S. Chem. Rev. 1989, 89, 1535
31. Matteson, D. S. Tetrahedron 1989, 45, 1859
32. Matteson, D. S. Tetrahedron 1998, 54, 10555
33. Chin, C. C. H.; Yeo, J. S. L.; Loh, Z. H.; Vittal, J. J.; Henderson, W.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1998, 3777
34. Beeby, A.; Bettington, S.; Fairlamb, I. J. S.; Goeta, A. E.; Kapdi, A. R.; Niemela, E. H.; Thompson, A. L New J. Chem. 2004, 28, 600
35. Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036