Copper-catalyzed N-N bond formation by homocoupling of ketoximes via n-o bond cleavage: Facile, mild, and efficient synthesis of azines

Synthesis

Volumn 44, Issue 10, 2012, Pages 1501-1506

  Zhao, Mi Na ^a   Liang, Hao ^a   Ren, Zhi Hui ^a   Guan, Zheng Hui ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

azine; copper; homocoupling; ketoxime; NaHSO 3

Indexed keywords

AZINE; BOND CLEAVAGES; BOND FORMATION; EFFICIENT SYNTHESIS; HIGH YIELD; HOMOCOUPLING; KETOXIME; KETOXIMES; NAHSO 3; SODIUM BISULFITE;

CATALYSIS; FUNCTIONAL GROUPS; NITROGEN COMPOUNDS;

COPPER;

ACETOPHENONE OXIME; ARYLETHYLKETOXIME DERIVATIVE; AZINE DERIVATIVE; BISULFITE; COPPER; IODINE DERIVATIVE; KETOXIME DERIVATIVE; NAPHTHALENE OXIME; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HOMOCOUPLING REACTION; MOLECULAR INTERACTION; PROCESS DEVELOPMENT; REACTION OPTIMIZATION; REDUCTION KINETICS; SYNTHESIS;

EID: 84859096100     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290779     Document Type: Article

References (39)

1. Ashani Y, Silman I. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. Rappoport Z, Liebman JF. Wiley New York: 2008; 609
2. Nakamura I, Iwata T, Zhang D, Terada M. Org. Lett.: 2012; 14 206
3. Ramn RS, Bosson J, Dez-Gonzlez S, Marion N, Nolan SP. J. Org. Chem.: 2010; 75 1197
4. Ganguly NC, Mondal P. Synthesis: 2010; 3705
5. Augustine JK, Atta RN, Ramappa BK, Boodappa C. Synlett: 2009; 3378
6. Maimone TJ, Buchwald SL. J. Am. Chem. Soc.: 2010; 132 9990
7. Nonappa PD, Pandurangan K, Maitra U, Wailes S. Org. Lett.: 2007; 9 2767
8. Feng X.-H, Zhang G.-Z, Chen C.-Q, Yang M.-Y, Xu X.-Y, Huang G.-S. Synth. Commun.: 2009; 39 1768
9. Abdelselam A, Meyer AG, Tuck KL. Synlett: 2009; 955
10. Wang L, Huang C, Cai C. Catal. Commun.: 2010; 11 532
11. Liu S, Liebeskind LS. J. Am. Chem. Soc.: 2008; 130 6918
12. Liu SB, Yu Y, Liebeskind LS. Org. Lett.: 2007; 9 1947
13. Tan Y, Hartwig JF. J. Am. Chem. Soc.: 2010; 132 3676
14. Gerfaud T, Neuville L, Zhu J. Angew. Chem. Int. Ed.: 2009; 48 572
15. Parthasarathy K, Jeganmohan M, Cheng C.-H. Org. Lett.: 2008; 10 325
16. Zaman S, Mitsuru K, Ab AD. Org. Lett.: 2005; 7 609
17. Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem.: 2011; 76 6159
18. Nanjundaswamy HM, Pasha MA. Synth. Commun.: 2007; 37 3417
19. Manikannan R, Venkatesan R, Muthusubramanian S, Yogeeswari P, Sriram D. Bioorg. Med. Chem. Lett.: 2010; 20 6920
20. Cohen R, Rybtchinski B, Gandelman M, Shimon LJ. W, Martin JM. L, Milstein D. Angew. Chem. Int. Ed.: 2003; 42 1949
21. Ferguson LN, Goodwin TC. J. Am. Chem. Soc.: 1949; 71 633
22. Tang W, Xiang Y, Tong A. J. Org. Chem.: 2009; 74 2163
23. Rajendiran N, Balasubramanian T. Spectrochim. Acta, Part A: 2007; 68 894
24. Lewis M, Glaser R. J. Org. Chem.: 2002; 67 1441
25. Nalwa HS, Kakuta A, Mukoh A. J. Appl. Phys.: 1993; 73 4743
26. Kurteva VB, Simeonov SP, Stoilova-Disheva M. Pharmacology & Pharmacy: 2011; 2 1; http://www.scirp.org/journal/pp/
27. Kuznetsova YA, Romakh VB. Appl. Biochem. Biotechnol.: 1996; 61 205
28. Cianga I, Ivanoiu M. Eur. Polym. J.: 2006; 42 1922
29. Euler WB, Cheng M, Zhao C. Chem. Mater.: 1999; 11 3702
30. Kesslen EC, Euler WB. Chem. Mater.: 1999; 11 336
31. Euler WB. Chem. Mater.: 1990; 2 209
32. Kolb VM, Kuffel AC, Spiwek HO, Janota TE. J. Org. Chem.: 1989; 54 2771
33. Brun P, Tenalglia A, Waegell B. Tetrahedron: 1985; 41 5019
34. Nanjundaswamy HM, Pasha MA. Synth. Commun.: 2007; 37 3417
35. Safari J, Gandomi-Ravandi S. Synth. Commun.: 2011; 41 645
36. Lee B, Lee KH, Cho J, Nam W, Hur NH. Org. Lett.: 2011; 13 6386
37. Laouiti A, Rammah MM, Rammah MB, Marrot J, Couty F, Evano G. Org. Lett.: 2012; 14 6
38. Narasaka K, Kitamura M. Eur. J. Org. Chem.: 2005; 4505
39. Narasaka K. Pure Appl. Chem.: 2002; 74 143