Highly efficient copper-catalyzed hydroacylation reaction of aldehydes with azodicarboxylates

Tetrahedron Letters

Volumn 52, Issue 44, 2011, Pages 5880-5883

  Qin, Yuancheng ^a   Peng, Qiang ^a   Song, Jinsheng ^a   Zhou, Dan ^a  

^a NANCHANG HANGKONG UNIVERSITY   (China)

Author keywords

Aldehydes; Azo compounds; Copper catalyst; Hydroacylation

Indexed keywords

ALDEHYDE; AZODICARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; COPPER ACETATE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NITROGEN BOND; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HYDROACYLATION;

EID: 80055008377     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.165     Document Type: Article

References (44)

1. (a) Nair, V.; Biju, A. T.; Mathew, S. C.; Babu, B. P. Chem. Asian J. 2008, 3, 810;
2. (b) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520.
3. (a) Shen, B.; Makley, D. M.; Johnston, J. N. Nature 2010, 465, 1027;
4. (b) Thansandote, P.; Chong, E.; Feldmann, K.; Lautens, M. J. Org. Chem. 2010, 75, 3495;
5. (c) Shen, H.; Xie, Z. J. Am. Chem. Soc. 2010, 132, 11473;
6. (d) Mantel, M. L. H.; Lindhardt, A. T.; Lupp, D.; Skrydstrup, T. Chem. Eur. J. 2010, 16, 5437;
7. (e) Wang, S.; Wang, Z.; Zheng, X. Chem. Commun. 2009, 7372.
8. (a) Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8, 2213;
9. (b) Otte, R. D.; Sakata, T.; Guzei, I. A.; Lee, D. Org. Lett. 2005, 7, 495;
10. (c) Nair, V.; Biju, A. T.; Abhilash, K. G.; Menon, R. S.; Suresh, E. Org. Lett. 2005, 7, 2121;
11. (d) Nair, V.; Biju, A. T.; Vinod, A. U.; Suresh, E. Org. Lett. 2005, 7, 5139.
12. (a) Zhu, R.; Zhang, D.; Wu, J.; Liu, C. Tetrahedron: Asymmetry 2007, 1655, 18;
13. (b) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342;
14. (c) Thomassigny, C.; Prim, D.; Greck, C. Tetrahedron Lett. 2006, 47, 1117;
15. (d) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167;
16. (e) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367;
17. (f) Erdik, E. Tetrahedron 2004, 60, 8747;
18. (g) Greck, C.; Drouillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 1377.
19. (a) Doleschall, G. Tetrahedron Lett. 1978, 19, 2131;
20. (b) Abarca, B.; Ballesteros, R.; Gonzalez, E.; Sancho, P.; Sepulveda, J.; Soriano, C. Heterocycles 1990, 31, 1811;
21. (c) Reliquet, A.; Besbes, R.; Reliquet, F.; Meslin, J. C. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 70, 211;
22. (d) Denis, A.; Renou, C. Tetrahedron Lett. 2002, 43, 4171.
23. (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556;
24. (b) Stephenson, L. M.; Mattern, D. J. Org. Chem. 1976, 41, 3614;
25. (c) Grigg, R.; Kemp, J. J. Chem. Soc., Chem. Commun. 1977, 125;
26. (d) Dang, H. S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721;
27. (e) Leblanc, Y.; Zamboni, R.; Bernstein, M. A. J. Org. Chem. 1991, 56, 1971;
28. (f) Brimble, M. A.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5261;
29. (g) Kinart, W. J. J. Chem. Res., Synop. 1994, 486;
30. (h) Sarkar, T. K.; Ghorai, B. K.; Das, S.; Grangopadhyay, P.; Rao, S. Tetrahedron Lett. 1996, 37, 6607;
31. (i) Aly, A. A.; Ehrhardt, S.; Hopf, H.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2006, 335;
32. (j) Biswas, A.; Sharma, B. K.; Willett, J. L.; Erhan, S. Z.; Cheng, H. N. Green Chem. 2008, 10, 298.
33. (a) Schenck, G. O.; Formaneck, H. Angew. Chem. 1958, 70, 505;
34. (b) Alder, K.; Noble, T. Ber. Dtsch. Chem. Ges. 1943, 54;
35. (c) Huisgen, R.; Jakob, F. Liebigs Ann. Chem. 1954, 590, 37;
36. (d) González-Rosende, M. E.; Lozano-Lucia, O.; Zaballos-Garcia, E.; Sepúlveda-Arques, J. J. Chem. Res., Synop. 1995, 260;
37. (e) Zaballos-García, E.; González-Rosende, M. E.; Jorda-Gregori, J. M.; Sepúlveda-Arques, J.; Jennings, W. B.; O'Leary, D.; Twomey, S. Tetrahedron 1997, 53, 9313.
38. (a) Lee, D.; Otte, R. D. J. Org. Chem. 2004, 69, 3569;
39. (b) Kim, Y. J.; Lee, D. Org. Lett. 2004, 6, 4351.
40. (a) Ni, B.; Zhang, Q.; Garre, S.; Headley, A. D. Adv. Synth. Catal. 2009, 351, 875;
41. (b) Zhang, Q.; Parker, E.; Headley, A. D.; Ni, B. Synlett 2010, 2453.
42. Chudasama, V.; Fitzmaurice, R. J.; Caddick, S. Nature Chem. 2010, 2, 592.
43. Metzger, J. O.; Mahler, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 902.
44. Ranu, B. C.; Saha, A.; Jana, R. Adv. Synth. Catal. 2007, 349, 2690.