Characterization and utility of N-unsubstituted imines synthesized from alkyl azides by ruthenium catalysis

Angewandte Chemie - International Edition

Volumn 51, Issue 43, 2012, Pages 10851-10855

  Lee, Jin Hee ^a   Gupta, Sreya ^a   Jeong, Wook ^a   Rhee, Young Ho ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

allylation; azides; imines; photochemistry; ruthenium

Indexed keywords

AZIDES; CHEMOSELECTIVE; CIS/TRANS ISOMERS; IMINE FORMATION; IMINES; ONE POT; RUTHENIUM CATALYSIS; SYNTHETIC METHODS; SYNTHETIC UTILITY; TITLE COMPOUNDS;

ALLYLATION; CATALYSIS; ISOMERS; PHOTOCHEMICAL REACTIONS; RUTHENIUM;

NITROGEN COMPOUNDS;

AZIDE; IMINE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; ISOMERISM; SYNTHESIS; ULTRAVIOLET RADIATION;

AZIDES; CATALYSIS; IMINES; ISOMERISM; RUTHENIUM; ULTRAVIOLET RAYS;

EID: 84867569537     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204483     Document Type: Article

References (32)

1. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569.
2. X.-Q. Zhu, Q.-Y. Liu, Q. Chen, L.-R. Mei, J. Org. Chem. 2010, 75, 789-808.
3. D. R. Boyd, R. Hamilton, N. T. Thompson, M. E. Stubbs, Tetrahedron Lett. 1979, 20, 3201-3204.
4. B. Bogdamoviç, D.-I. M. Veliç, Angew. Chem. 1967, 79, 818-819
5. Angew. Chem. Int. Ed. Engl. 1967, 6, 803-807.
6. G.-M. Chen, H. C. Brown, J. Am. Chem. Soc. 2000, 122, 4217-4218.
7. S. Itsuno, K. Watanabe, T. Matsumoto, S. Kuroda, A. Yokoi, A. El-Shehawy, J. Chem. Soc. Perkin Trans. 1 1999, 2011-2016.
8. Y. Bergman, P. Perlmutter, N. Thienthong, Green Chem. 2004, 6, 539-540.
9. M. Sugiura, K. Hirano, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7182-7183.
10. B. Dhudshia, J. Tiburcio, A. N. Thadani, Chem. Commun. 2005, 5551-5553.
11. P. V. Ramachandran, T. E. Burghardt, Pure Appl. Chem. 2006, 78, 1397-1406.
12. T. R. Ramadhar, R. A. Batey, Synthesis 2011, 1321-1346.
13. P. V. Ramachandran, D. Biswas, Org. Lett. 2007, 9, 3025-3027.
14. G. Hou, F. Gosselin, J. Am. Chem. Soc. 2009, 131, 9882-9883.
15. S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320-5374
16. Angew. Chem. Int. Ed. 2005, 44, 5188-5240.
17. G. Albertin, S. Antoniutti, D. Baldan, J. Castro, S. García- Fontán, Inorg. Chem. 2008, 47, 742-748.
18. G. Albertin, S. Antoniutti, J. Castro, J. Organomet. Chem. 2010, 695, 574-579.
19. S. Chiba, L. Zhang, J.-Y. Lee, J. Am. Chem. Soc. 2010, 132, 7266-7267.
20. R. A. Lewis, G. Wu, T. W. Hayton, J. Am. Chem. Soc. 2010, 132, 12814-12816.
21. E. P. Kyba, R. A. Abramovitch, J. Am. Chem. Soc. 1980, 102, 735-740.
22. J. Risse, R. Scopelliti, K. Severin, Organometallics 2011, 30, 3412-3418.
23. Y. Do, I.-C. Hwang, M.-J. Kim, J. Park, J. Org. Chem. 2010, 75, 5740-5742.
24. Y. Do, J. Han, Y. H. Rhee, J. Park, Adv. Synth. Catal. 2011, 353, 3363-3366.
25. C. P. Casey, T. E. Vos, S. W. Singer, I. A. Guzei, Organometallics 2002, 21, 5038-5046.
26. J.-M. Huang, J.-F. Zhang, Y. Dong, W. Gong, J. Org. Chem. 2011, 76, 3511-3514.
27. T. K. Ha, H. H. Gunthard, J. Mol. Struct. 1992, 95, 187-208.
28. Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603-1662.
29. H. Ren, W. D. Wulff, J. Am. Chem. Soc. 2011, 133, 5656-5659.
30. M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 10244-10247
31. Angew. Chem. Int. Ed. 2008, 47, 10090-10093.
32. J. Nyhlén, T. Priovalov, J.-E. Bäckvall, Chem. Eur. J. 2009, 15, 5220-5229.