Development of a palladium-catalyzed α-arylation of cyclopropyl nitriles

Organic Letters

Volumn 16, Issue 24, 2014, Pages 6314-6317

  McCabe Dunn, Jamie M ^a   Kuethe, Jeffrey T ^a   Orr, Robert K ^a   Tudge, Matthew ^a   Campeau, Louis Charles ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84919684164     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5030426     Document Type: Article

References (39)

1. Chen, D. Y.-K.; Pouwer, R. H.; Richard, J.-A. Chem. Soc. Rev. 2012, 41, 4631
2. de Meijere, A.; Hadjiarapoglou, L. P.; Iwasawa, N.; Khlebnikov, A. F.; Kozhushkov, S. I.; Narasaka, K.; Salaün, J. Small Ring Compounds in Organic Synthesis VI. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer-Verlag: Berlin, 2000; Vol. 207, p 3.
3. Gagnon, A.; Duplessis, M.; Fader, L. Org. Prep. Proced. Int. 2010, 42, 1
4. Nowak, G.; Pomierny-Chamioło, L.; Siwek, A.; Niedzielska, E.; Pomierny, B.; Pałucha-Poniewiera, A.; Pilc, A. Neuropharmacology 2014, 84, 46
5. Burch, J. D.; Belley, M.; Fortin, R.; Deschênes, D.; Girard, M.; Colucci, J.; Farand, J.; Therien, A. G.; Mathieu, M.-C.; Denis, D.; Vigneault, E.; Lévesque, J.-F.; Gagné, S.; Wrona, M.; Xu, D.; Clark, P.; Rowland, S.; Han, Y. Bioorg. Med. Chem. Lett. 2008, 18, 2048
6. Komine, T.; Kojima, A.; Asahina, Y.; Saito, T.; Takano, H.; Shibue, T.; Fukuda, Y. J. Med. Chem. 2008, 51, 6558
7. Hadida-Ruah, S.; Hamilton, M.; Miller, M.; Grootenhuis, P. D. J.; Bear, B.; McCartney, J.; Zhou, J.; van Goor, F. Modulators of ATP-Binding Cassette Transporters. U.S. Pat. Appl. Publ. 20080019915, 2008.
8. Yan, L.; Huo, P.; Hale, J. J.; Mills, S. G.; Hajdu, R.; Keohane, C. A.; Rosenbach, M. J.; Milligan, J. A.; Shei, G.-J.; Chrebet, G.; Bergstrom, J.; Card, D.; Mandala, S. M. Bioorg. Med. Chem. Lett. 2007, 17, 828
9. Gagnon, A.; Amad, M. H.; Bonneau, P. R.; Coulombe, R.; DeRoy, P. L.; Doyon, L.; Duan, J.; Garneau, M.; Guse, I.; Jakalian, A.; Jolicoeur, E.; Landry, S.; Malenfant, E.; Simoneau, B.; Yoakim, C. Bioorg. Med. Chem. Lett. 2007, 17, 4437
10. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977
11. Papahatjis, D. P.; Nikas, S.; Tsotinis, A.; Vlachou, M.; Makriyannis, A. Chem. Lett. 2001, 3, 192
12. Arava, V. R.; Siripalli, U. B. R.; Dubey, P. K. Tetrahedron Lett. 2005, 46, 7247
13. Barbasiewicz, M.; Marciniak, K.; Fedoryński, M. Tetrahedron Lett. 2006, 47, 3871
14. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611
15. Clemens, J. J.; Asgian, J. L.; Busch, B. B.; Coon, T.; Ernst, J.; Kaljevic, L.; Krenitsky, P. J.; Neubert, T. D.; Schweiger, E. J.; Termin, A.; Stamos, D. J. Org. Chem. 2013, 78, 780
16. For a review, see: Gololobov, Y. G.; Nesmeyanov, A. N.; Lysenko, V. P.; Boldeskul, I. E. Tetrahedron 1987, 43, 2609
17. Klapars, A.; Waldman, J. H.; Campos, K. R.; Jensen, M. S.; Mclaughlin, M.; Chung, J. Y. L.; Cvetovich, R. J.; Chen, C. J. Org. Chem. 2005, 70, 10186
18. Caron, S.; Vazquez, E.; Wojcik, J. M. J. Am. Chem. Soc. 2000, 122, 712
19. For a recent review, see: Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676
20. You, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5051
21. You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003
22. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330
23. Duez, S.; Bernhardt, S.; Heppekausen, J.; Fleming, F. F.; Knochel, P. Org. Lett. 2011, 13, 1690
24. Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932
25. Cyclopropyl nitrile is found to have lower acidity and a unique carbanion structure and reactivity when compared to acyclic and larger ring cyclic nitriles. See: Juchnovski, I. N.; Tsenov, J. A.; Binev, I. G. Spectrochim. Acta Part A 1996, 52, 1145
26. To our knowledge, the direct Pd-catalyzed α-arylation of cyclopropyl-derived nitriles or cyclopropyl esters has not been reported. For a report on deprotonation kinetics of cyclopropanes, see: Van Wunen, W. Th.; Steinberg, H.; De Boer, TH. J. Tetrahedron 1972, 28, 5423
27. Hama, T.; Ge, S.; Hartwig, J. F. J. Org. Chem. 2013, 78, 8250
28. Hama, T.; Hartwig, J. F. Org. Lett. 2008, 10, 1545
29. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257
30. Schultz, S. C.; Krska, S. W. Acc. Chem. Res. 2007, 40, 1320
31. Schmink, J. R.; Bellomo, A.; Berritt, S. Aldrichimica Acta 2013, 46, 71
32. Unsuccessful reactions employing 2b may be due to the instability of the deprotonated ester at elevated temperatures; see: Häner, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1655
33. Phenolic silyl ethers cleave more readily than alkyl silyl ethers under basic conditions; see: Collington, E. W.; Finch, H.; Smith, I. J. Tetrahedron Lett. 1985, 26, 681
34. Papahatjis, D. P.; Nahmias, V. R.; Nikas, S. P.; Andreou, T.; Alapafuja, S. O.; Tsotinis, A.; Guo, J.; Fan, P.; Makriyannis, A. J. Med. Chem. 2007, 50, 4048
35. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
36. Sandanayaka, V.; Singh, J.; Gurney, M.; Mamat, B.; Yu, P.; Bedel, L.; Zhao, L. Biaryl substituted heterocycle inhibitors of LTA4H for treating inflammation. U.S. Pat. Appl. Publ. 20070066820, 2007.
37. Chin, E.; De Vicente Fidalgo, J.; Li, J.; Jui, A. S-T.; McCaleb, K. L.; Schoenfeld, R. C.; Talamas, F. X. Heterocyclic antiviral compound. WO2010149598, 2010.
38. Barnes-Seeman, D.; Jain, M.; Bell, L.; Ferreira, S.; Cohen, S.; Chen, X.-H.; Amin, J.; Snodgrass, B.; Hatsis, P. ACS Med. Chem. Lett. 2013, 4, 514
39. During the preparation of this manuscript, a method for the direct installation of this functional group via a radical pathway was described; see: Gianatassio, R.; Kawamura, S.; Eprile, C. L.; Foo, K.; Ge, J.; Burns, A. C.; Collins, M. R.; Baran, P. S. Angew. Chem., Int. Ed. 2014, 53, 9851