Engaging nonaromatic, heterocyclic tosylates in reductive cross-coupling with aryl and heteroaryl bromides

Journal of Organic Chemistry

Volumn 80, Issue 5, 2015, Pages 2907-2911

  Molander, Gary A ^a   Traister, Kaitlin M ^a   O'Neill, Brian T ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ORGANIC COMPOUNDS;

CROSS-COUPLINGS; CRYSTALLINE SOLIDS; HETEROCYCLIC STRUCTURES;

SULFUR COMPOUNDS;

ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; CRYSTALLIN;

ARTICLE; CATALYST; CROSS COUPLING REACTION; MELTING POINT; REACTION OPTIMIZATION; REDUCTION; SOLID; STOICHIOMETRY;

EID: 84924325585     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00135     Document Type: Article

References (40)

1. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920
2. Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146
3. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192
4. Everson, D. A.; Buonomo, J. A.; Weix, D. J. Synlett 2014, 25, 233
5. Gomes, P.; Gosmini, C.; Perichon J. Org. Lett. 2013, 5, 1043
6. Gosmini, C.; Bassene-Ernst, C.; Durandetti, M. Tetrahedron 2009, 65, 6141
7. Durandetti, M.; Nedelec, J.-Y.; Perichon, J. J. Org. Chem. 1996, 61, 1748
8. Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442
9. Leon, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221
10. Yan, C.-S.; Peng, Y.; Xu, X.-B.; Wang, Y.-W. Chem.-Eur. J. 2012, 18, 6039
11. Durandetti, M.; Gosmini, C.; Perichon, J. Tetrahedron 2007, 63, 1146
12. Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793
13. Liu, D.; Liu, C.; Li, H.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 4453
14. Gartia, Y.; Ramidi, P.; Jones, D. E.; Pulla, S.; Ghosh, A. Catal. Lett. 2014, 144, 507
15. Millet, A.; Larini, P.; Clot, E.; Baudoin, O. Chem. Sci. 2013, 4, 2241
16. Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774
17. Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756
18. Nakamura, M.; Ito, S.; Matsuo, K.; Nakamura, E. Synlett 2005, 11, 1794
19. Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556
20. Duncton, M. A. J.; Estiarte, M. A.; Tan, D.; Kaub, C.; O'Mahony, D. J. R.; Johnson, R. J.; Cox, M.; Edwards, W. T.; Wan, M.; Kincaid, J.; Kelly, M. G. Org. Lett. 2008, 10, 3259
21. Pompeo, M.; Froese, R. D. J.; Hadei, N.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 11354
22. Han, C.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 7532
23. Corley, E. G.; Conrad, K.; Murry, J. A.; Savarin, C.; Holko, J.; Boice, G. J. Org. Chem. 2004, 69, 5120
24. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592
25. Duplais, C.; Krasovskiy, A.; Lipshutz, B. H. Organometallics 2011, 30, 6090
26. Melzig, L.; Gavryushin, A.; Knochel, P. Org. Lett. 2007, 9, 5529
27. Li, L.; Wang, C.-Y.; Huang, R.; Biscoe, M. R. Nat. Chem. 2013, 5, 607
28. Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138
29. Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022
30. Wang, S.; Qian, Q.; Gong, H. Org. Lett. 2012, 14, 3352
31. Molander, G. A.; Traister, K. M.; O'Neill, B. T. J. Org. Chem. 2014, 79, 5771
32. Katz, J. D.; Jewell, P.; Guerin, D. J.; Lim, J.; Dinsmore, C. J.; Deshmukh, S. V.; Pan, B.-S.; Marshall, C. G.; Lu, W.; Altman, M. D.; Dahlberg, W. K.; Davis, L.; Falcone, D.; Gabarda, A. E.; Hang, G.; Hatch, H.; Holmes, R.; Kunii, K.; Lumb, K. J.; Lutterbach, B.; Mathvink, R.; Nazef, N.; Patel, S. B.; Qu, X.; Reilly, J. F.; Rickert, K. W.; Rosenstein, C.; Soisson, S. M.; Spencer, K. B.; Szewczak, A. A.; Walker, D.; Wang, W.; Young, J.; Zeng, Q. J. Med. Chem. 2011, 54, 4092
33. Liu, J.-H.; Yang, C.-T.; Lu, X.-Y.; Zhang, Z.-Q.; Xu, L.; Cui, M.; Lu, X.; Xioa, B.; Fu, Y.; Liu, L. Chem.-Eur. J. 2014, 20, 15334
34. Liang, Z.; Xue, W.; Lin, K.; Gong, H. Org. Lett. 2014, 16, 5620
35. Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022
36. Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743
37. Ackerman, L. K. G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Chem. Sci. 2015, 6, 1115
38. Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627
39. Zembayashi, M.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 18, 4089
40. Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645