Reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl and heteroaryl bromides

Journal of Organic Chemistry

Volumn 79, Issue 12, 2014, Pages 5771-5780

  Molander, Gary A ^a   Traister, Kaitlin M ^a   ONeill, Brian T ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLICS;

AIR-STABLE; ARYL HALIDES; C-C BOND FORMATION; CROSS-COUPLINGS; DIAMINE LIGANDS; HETEROCYCLIC RINGS; ORGANIC HALIDES; ORGANOMETALLIC REAGENT;

CHEMICAL REACTIONS;

3 (TETRAHYDRO 2 H PYRAN 4 YL)QUINOLINE; 5 (TETRAHYDRO 2H PYRAN 4 YL) 1H PYRROLO[2,3 B]PYRIDINE; 5 (TETRAHYDRO 2H PYRAN 4 YL)BENZOFURAN; BROMINE DERIVATIVE; COPPER; HETEROCYCLIC COMPOUND; IODIDE; LEAD; NICKEL; ORGANOHALOGEN DERIVATIVE; TERT BUTYL 3 (QUINOLIN 3 YL)AZETIDINE 1 CARBOXYLATE; TERT BUTYL 4 (1H INDAL 5 YL)PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 (ISOQUINOLIN 4 YL)PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 (QUINOLIN 3 YL)PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 (QUINOXALIN 4 YL)PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 [4 (1,3,4 OXADIAZOL 2 YL)PHENYL]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 5 (OXETAN 3 YL) 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 5 (TETRAHYDRO 2H PYRAN 4 YL) 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 5 (TETRAHYDRO 3 YL) 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 5 [1 (TERT BUTOXYCARBONYL)AZETIDIN 3 YL] 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 5 [1 (TERT BUTOXYCARBONYL)PIPERIDIN 3 YL] 1H INDOLE 1 CARBOXYLATE; TERT BUTYL 5 [1 (TERT BUTOXYCARBONYL)PYRROLIDIN 3 YL] 1H INDOLE 1 CARBOXYLATE; TETR BUTYL 5 [1 (TERT BUTOXYCARBONYL)PIPERIDINE 4 YL] 1H INDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG; BROMIDE; CROSS LINKING REAGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LIGAND; METAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CROSS COUPLING REACTION; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

BROMIDES; CATALYSIS; CROSS-LINKING REAGENTS; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; LIGANDS; METALS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84903156770     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500905m     Document Type: Article

References (42)

1. Loverling, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752
2. Allwood, D. M.; Blakemore, D. C.; Brown, A. D.; Ley, S. V. J. Org. Chem. 2014, 79, 328
3. Aikawa, H.; Tago, S.; Umetsu, K.; Haginiwa, N.; Asao, N. Tetrahedron 2009, 65, 1774
4. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Ito, S. Tetrahedron Lett. 1996, 37, 2463
5. Diba, A. K.; Begouin, J.-M.; Niggemann, M. Tetrahedron Lett. 2012, 53, 6629
6. Schmidle, C. J.; Mansfield, R. C. J. Am. Chem. Soc. 1956, 78, 1702
7. Li, G.; Zhou, H.; Jiang, Y.; Keim, H.; Topiol, S. W.; Poda, S. B.; Ren, Y.; Chandrasena, G.; Doller, D. Bioorg. Med. Chem. Lett. 2011, 21, 1236
8. Wang, X.; Kauppi, A. M.; Olsson, R.; Almqvist, F. Eur. J. Org. Chem. 2003, 4586
9. Liu, D.; Liu, C.; Li, H.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 4453
10. Gartia, Y.; Ramidi, P.; Jones, D. E.; Pulla, S.; Ghosh, A. Catal. Lett. 2014, 144, 507
11. Millet, A.; Larini, P.; Clot, E.; Baudoin, O. Chem. Sci. 2013, 4, 2241
12. Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774
13. Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756
14. Nakamura, M.; Ito, S.; Matsuo, K.; Nakamura, E. Synlett 2005, 11, 1794
15. Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556
16. Duncton, M. A. J.; Estiarte, M. A.; Tan, D.; Kaub, C.; OMahony, D. J. R.; Johnson, R. J.; Cox, M.; Edwards, W. T.; Wan, M.; Kincaid, J.; Kelly, M. G. Org. Lett. 2008, 10, 3259
17. Pompeo, M.; Froese, R. D. J.; Hadei, N.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 11354
18. Han, C.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 7532
19. Corley, E. G.; Conrad, K.; Murry, J. A.; Savarin, C.; Holko, J.; Boice, G. J. Org. Chem. 2004, 69, 5120
20. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592
21. Duplais, C.; Krasovskiy, A.; Lipshutz, B. H. Organometallics 2011, 30, 6090
22. Melzig, L.; Gavryushin, A.; Knochel, P. Org. Lett. 2007, 9, 5529
23. Li, L.; Wang, C.-Y.; Huang, R.; Biscoe, M. R. Nat. Chem. 2013, 5, 607
24. Presset, M.; Fleury-Bregeot, N.; Oehlrich, D.; Rombouts, F.; Molander, G. A. J. Org. Chem. 2013, 78, 4615
25. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920
26. Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146
27. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192
28. Everson, D. A.; Buonomo, J. A.; Weix, D. J. Synlett 2014, 25, 233
29. Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138
30. Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022
31. Wang, S.; Qian, Q.; Gong, H. Org. Lett. 2012, 14, 3352
32. Gomes, P.; Gosmini, C.; Perichon, J. Org. Lett. 2013, 5, 1043
33. Gosmini, C.; Bassene-Ernst, C.; Durandetti, M. Tetrahedron 2009, 65, 6141
34. Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748
35. Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442
36. Leon, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221
37. Yan, C.-S.; Peng, Y.; Xu, X.-B.; Wang, Y.-W. Chem.-Eur. J. 2012, 18, 6039
38. Durandetti, M.; Gosmini, C.; Périchon, J. Tetrahedron 2007, 63, 1146
39. Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 10.1012/jo500507s
40. Molander, G. A.; Cavalcanti, L. N.; Garcia-Garcia, C. J. Org. Chem. 2013, 78, 6427
41. Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627
42. Zembayashi, M.; Tamao, K.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 18, 4089