Transition-metal-free direct alkylation of aryl tetrazoles via intermolecular oxidative C-N formation

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11780-11786

  Wang, Liang ^a   Zhu, Kaiqiang ^a   Chen, Qun ^a   He, Mingyang ^a  

^a CHANGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS;

ALKYL ETHERS; BENZYLIC; C-H ACTIVATION; C-N BOND FORMATIONS; DIRECT ALKYLATION; SYNTHETIC APPROACH; TETRAZOLES;

TRANSITION METALS;

ALKYL ETHER; CARBON; NITROGEN; OXIDIZING AGENT; TETRAZOLE DERIVATIVE; TOLUENE; TRANSITION ELEMENT; BENZYL DERIVATIVE; METAL;

ALKYLATION; AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL BOND; CONTROLLED STUDY; MASS SPECTROMETRY; OXIDATION; OXIDATIVE COUPLING; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYLATION; BENZYL COMPOUNDS; CATALYSIS; HYDROGEN BONDING; METALS; MOLECULAR STRUCTURE; OXIDANTS; OXIDATION-REDUCTION; TETRAZOLES; TRANSITION ELEMENTS;

EID: 84916217239     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502283h     Document Type: Article

References (40)

1. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH Publishers: New York, 1989.
2. Fernandez-Bachiller, M. I.; Perez, C.; Monjas, L.; Rademann, J.; Rodríguez-Franco, M. I. J. Med. Chem. 2012, 55, 1303
3. Das, S. G.; Srinivasan, B.; Hermanson, D. L.; Bleeker, N. P.; Doshi, J. M.; Tang, R.; Beck, W. T.; Xing, C. J. Med. Chem. 2011, 54, 5937
4. Aromí, G.; Barrios, L. A.; Roubeau, O.; Gamez, P. Coord. Chem. Rev. 2011, 255, 485
5. Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584
6. Tao, G. H.; Guo, Y.; Joo, Y. H.; Twamley, B.; Shreeve, J. M. J. Mater. Chem. 2008, 18, 5524
7. Birnbaum, J.; Kahan, F. M.; Kropp, H. Am. J. Med. 1985, 78, 3
8. Seki, M. ACS Catal. 2011, 1, 607
9. Diers, E.; Kumar, N. Y. P.; Mejuch, T.; Marek, I.; Ackermann, L. Tetrahedron 2013, 69, 4445
10. Wang, L.; Wu, W. T.; Chen, Q.; He, M. Y. Org. Biomol. Chem. 2014, 12, 7923
11. Aridoss, G.; Laali, K. K. Eur. J. Org. Chem. 2011, 6343
12. Li, C. J. Acc. Chem. Res. 2009, 42, 335
13. Scheuermann, C. J. Chem.-Asian J. 2010, 5, 436
14. Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74
15. Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827
16. Ma, L.; Wang, X.; Yu, W.; Han, B. Chem. Commun. 2011, 47, 11333
17. Froehr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.; Nachtsheim, B. J. Org. Lett. 2011, 13, 3754
18. Uyanik, M.; Ishihara, K. ChemCatChem 2012, 4, 177
19. Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231
20. Mai, W.; Wang, H.; Li, Z.; Yuan, J.; Xiao, Y.; Yang, L.; Mao, P.; Qu, L. Chem. Commun. 2012, 48, 10117
21. Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538
22. Li, L.; Huang, J.; Li, H.; Wen, L.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187
23. Xie, J.; Jiang, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2012, 48, 979
24. Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376
25. Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331
26. Chen, L.; Shi, E.; Liu, Z.; Chen, S.; Wei, W.; Li, H.; Xu, K.; Wan, X. Chem.-Eur. J. 2011, 17, 4085
27. Huang, J.; Li, L.; Li, H.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204
28. Shi, E.; Chen, S.; Chen, S.; Hu, H.; Chen, S.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384
29. Feng, J.; Liang, S.; Chen, S.; Zhang, J.; Fu, S.; Yu, X. Adv. Synth. Catal. 2012, 354, 1287
30. Dian, L.; Wang, S.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Chem. Commun. 2014, 50, 11738
31. Guo, S.; Yu, J.; Dai, Q.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 6240
32. Xue, Q.; Li, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 3700
33. Ochiai, M.; Yamane, S.; Hoque, M. M.; Saito, M.; Miyamoto, K. Chem. Commun. 2012, 48, 5280
34. Pan, S.; Liu, J.; Li, H.; Wang, Z.; Guo, X.; Li, Z. Org. Lett. 2010, 12, 1932
35. He, L.; Yu, J.; Zhang, J.; Yu, X.-Q. Org. Lett. 2007, 9, 2277
36. Bhuyan, R.; Nicholas, K. M. Org. Lett. 2007, 9, 3957
37. Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784
38. Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233
39. Ali, W.; Guin, S.; Rout, S. K.; Gogoi, A.; Patel, B. K. Adv. Synth. Catal. 2014, 356, 3099
40. Han, F.; Yang, L.; Li, Z.; Xia, C. Adv. Synth. Catal. 2012, 354, 1052