Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(10): 1501-1506
DOI: 10.1055/s-0031-1290779
DOI: 10.1055/s-0031-1290779
special topic
Copper-Catalyzed N–N Bond Formation by Homocoupling of Ketoximes via N–O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines
Further Information
Publication History
Received: 03 February 2012
Accepted: 05 March 2012
Publication Date:
30 March 2012 (online)
Abstract
A facile, mild, and efficient copper-catalyzed homocoupling of ketoximes involving N–O bond cleavage in the presence of sodium bisulfite (NaHSO3) has been developed. This reaction shows good functional group tolerance and affords a broad scope of azines in high yields.
-
References
- 1 Ashani Y, Silman I In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids . Rappoport Z, Liebman JF. Wiley; New York: 2008: 609
- 2a Nakamura I, Iwata T, Zhang D, Terada M. Org. Lett. 2012; 14: 206
- 2b Ramón RS, Bosson J, Díez-González S, Marion N, Nolan SP. J. Org. Chem. 2010; 75: 1197
- 2c Ganguly NC, Mondal P. Synthesis 2010; 3705
- 2d Augustine JK, Atta RN, Ramappa BK, Boodappa C. Synlett 2009; 3378
- 3 Ren Z.-H, Zhang Z.-Y, Yang B.-Q, Wang Y.-Y, Guan Z.-H. Org. Lett. 2011; 13: 5394 ; and references therein
- 4a Maimone TJ, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 9990
- 4b Nonappa PD, Pandurangan K, Maitra U, Wailes S. Org. Lett. 2007; 9: 2767
- 4c Feng X.-H, Zhang G.-Z, Chen C.-Q, Yang M.-Y, Xu X.-Y, Huang G.-S. Synth. Commun. 2009; 39: 1768
- 4d Abdelselam A, Meyer AG, Tuck KL. Synlett 2009; 955
- 4e Wang L, Huang C, Cai C. Catal. Commun. 2010; 11: 532
- 5a Liu S, Liebeskind LS. J. Am. Chem. Soc. 2008; 130: 6918
- 5b Liu SB, Yu Y, Liebeskind LS. Org. Lett. 2007; 9: 1947
- 6a Tan Y, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 3676
- 6b Gerfaud T, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2009; 48: 572
- 6c Parthasarathy K, Jeganmohan M, Cheng C.-H. Org. Lett. 2008; 10: 325
- 6d Zaman S, Mitsuru K, Ab AD. Org. Lett. 2005; 7: 609
-
6e Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem. 2011; 76: 6159
- 7 Guan Z.-H, Zhang Z.-Y, Ren Z.-H, Wang Y.-Y, Zhang X. J. Org. Chem. 2011; 76: 339
- 8a Nanjundaswamy HM, Pasha MA. Synth. Commun. 2007; 37: 3417
- 8b Manikannan R, Venkatesan R, Muthusubramanian S, Yogeeswari P, Sriram D. Bioorg. Med. Chem. Lett. 2010; 20: 6920
- 8c Cohen R, Rybtchinski B, Gandelman M, Shimon LJ. W, Martin JM. L, Milstein D. Angew. Chem. Int. Ed. 2003; 42: 1949
- 8d Ferguson LN, Goodwin TC. J. Am. Chem. Soc. 1949; 71: 633
- 9a Tang W, Xiang Y, Tong A. J. Org. Chem. 2009; 74: 2163
- 9b Rajendiran N, Balasubramanian T. Spectrochim. Acta, Part A 2007; 68: 894
- 9c Lewis M, Glaser R. J. Org. Chem. 2002; 67: 1441
- 9d Nalwa HS, Kakuta A, Mukoh A. J. Appl. Phys. 1993; 73: 4743
- 10a Kurteva VB, Simeonov SP, Stoilova-Disheva M. Pharmacology & Pharmacy 2011; 2: 1 ; http://www.scirp.org/journal/pp/
- 10b Kuznetsova YA, Romakh VB. Appl. Biochem. Biotechnol. 1996; 61: 205
- 11a Cianga I, Ivanoiu M. Eur. Polym. J. 2006; 42: 1922
- 11b Euler WB, Cheng M, Zhao C. Chem. Mater. 1999; 11: 3702
- 11c Kesslen EC, Euler WB. Chem. Mater. 1999; 11: 336
- 11d Euler WB. Chem. Mater. 1990; 2: 209
- 12 Wu CY, Chen Y, Jing SY, Lee CS, Dinda J, Hwang WS. Polyhedron 2006; 25: 3053
- 13a Kolb VM, Kuffel AC, Spiwek HO, Janota TE. J. Org. Chem. 1989; 54: 2771
- 13b Brun P, Tenalglia A, Waegell B. Tetrahedron 1985; 41: 5019
- 13c Nanjundaswamy HM, Pasha MA. Synth. Commun. 2007; 37: 3417
- 13d Safari J, Gandomi-Ravandi S. Synth. Commun. 2011; 41: 645
- 14a Lee B, Lee KH, Cho J, Nam W, Hur NH. Org. Lett. 2011; 13: 6386
- 14b Laouiti A, Rammah MM, Rammah MB, Marrot J, Couty F, Evano G. Org. Lett. 2012; 14: 6
- 15a Narasaka K, Kitamura M. Eur. J. Org. Chem. 2005; 4505
- 15b Narasaka K. Pure Appl. Chem. 2002; 74: 143
- 16 Zhao H, Vandenbossche CP, Koenig SG, Singh SP, Bakale RP. Org. Lett. 2008; 10: 505