Catalytic formal [4 + 2] cycloadditions between unactivated allenes and N-hydroxyaniline catalyzed by AuCl3/CuCl2/O2

Journal of Organic Chemistry

Volumn 79, Issue 10, 2014, Pages 4306-4311

  Chen, Jian Ming ^a   Chang, Chin Jung ^a   Ke, Yao Jin ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYTIC OXIDATION; ISOMERIZATION;

ALLENES; CYCLOADDITIONS; NITROSO; NITROSOARENES; OXIDATION EFFICIENCY; REACTION SEQUENCES;

HYDROCARBONS;

1,3 BUTADIENE DERIVATIVE; ALKADIENE; ALLENE DERIVATIVE; ANILINE DERIVATIVE; COPPER CHLORIDE; GOLD CHLORIDE; N HYDROXYANILINE; NITROSOARENE DERIVATIVE; NITROSOBENZENE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; CYCLOADDITION; ENANTIOSELECTIVITY; ISOMERIZATION; OXIDATION;

EID: 84900838598     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500009x     Document Type: Article

References (42)

1. Bodnar, B. S.; Miller, M. J. Angew. Chem., Int. Ed. 2011, 50, 5630
2. Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087
3. Yamamoto, Y.; Yamamoto, H. Eur. J. Org. Chem. 2006, 2031
4. Yamamoto, H.; Kawasaki, M. Bull. Chem. Soc. Jpn. 2007, 80, 595
5. Zhang, D.; Sueling, C.; Miller, M. J. J. Org. Chem. 1998, 63, 885
6. Ware, R. W.; Day, C. S.; King, S. B. J. Org. Chem. 2002, 67, 6174
7. Miller, C. A.; Batey, R. A. Org. Lett. 2004, 6, 699
8. Yamamoto, H.; Momiyama, N. Chem. Commun. 2005, 3514
9. Moyiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 1080
10. Jana, C. K.; Studer, A. Angew. Chem., Int. Ed. 2007, 46, 6542
11. Barton, D. H. R.; Lester, D. J.; Ley, S. V. Chem. Commun. 1978, 276
12. Cicchi, S.; Corst, M.; Goti, A. J. Org. Chem. 1999, 64, 7243
13. Cicchi, S.; Marradi, M.; Goti, A.; Brandi, A. Tetrahedron Lett. 2001, 42, 6503
14. Adam, W.; Krebs, O. Chem. Rev. 2003, 103, 4131
15. Frazier, C. P.; Engelking, J. R.; Read de Alaniz, J. J. Am. Chem. Soc. 2011, 133, 10430
16. Chaiyaveij, D.; Cleary, L.; Batsanov, A. S.; Marder, T. B.; Shea, K. J.; Whiting, A. Org. Lett. 2011, 13, 3442
17. Frazier, C. P.; Bulgarin, A.; Engelking, J. R.; de Alaniz, J. R. Org. Lett. 2012, 14, 3620
18. Ting, C.-M.; Hsu, Y.-L.; Liu, R.-S. Chem. Commun. 2012, 48, 6577
19. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
20. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
21. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
22. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
23. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
24. Sohel, S. M. A.; Liu, R.-S. Chem. Soc. Rev. 2009, 38, 2269
25. López, F.; Mascareńas, J. L. Beilstein J. Org. Chem. 2011, 7, 1075
26. Garayalde, D.; Nevado, C. ACS Catal. 2012, 2, 1462
27. Binder, J. T.; Crone, B.; Haug, T. T.; Menz, H.; Kirsh, S. F. Org. Lett. 2008, 10, 1025
28. Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 48, 8923
29. Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796
30. Han, Z.-Y.; Xiao, H.; Chen, X. H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182
31. Monge, D.; Jensen, K. L.; Franke, P. T.; Lykke, L.; Jørgensen, K. A. Chem.-Eur. J. 2010, 16, 9478
32. Loh, C. C. J.; Badorrek, J.; Raabe, G.; Enders, D. Chem.-Eur. J. 2011, 17, 13409
33. Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C.; Gong, L.-Z. J. Am. Chem. Soc. 2012, 134, 6532
34. Kresze, G.; Firl, J. Tetrahedron 1968, 1043
35. Sasaki, T.; Eguchi, S. J. Org. Chem. 1970, 35, 4273
36. Leach, A. G.; Houk, K. N. J. Org. Chem. 2001, 66, 5192
37. Meekel, A. A. P.; Resmini, M.; Pandit, U. K. Chem. Commun. 1995, 571-572
38. Resmini, M.; Meekel, A. A. P.; Pandit, U. K. Pure Appl. Chem. 1996, 68, 2025
39. Lutz, R. E.; Lytton, M. R. J. Org. Chem. 1937, 2, 68
40. Wang, Y.; Ye, L.; Zhang, L. Chem. Commun. 2011, 47, 7815
41. Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777
42. For the use of pyridine N -oxide as a proton shuttle, see: Wang, W.; Kumar, M.; Hammond, G. B.; Xu, B. Org. Lett. 2014, 16, 636