Nitorodecarboxylation 2016

Abstract

An additive-free, facile, efficient, and ecofriendly protocol for synthesis of (E)-nitroolefins via nitrodecarboxylation of α,β-unsaturated acids has been developed. Cu(NO₃)₂ was used as both nitrating agent and catalyst. Furthermore, the presented methodology offers several advantages such as easily accessible and stable substrates, inexpensive catalyst, high to excellent yield, short reaction time, and simple post treatment procedure.

Graphical Abstract

Keywords

Nitrodecarboxylationα,β-Unsaturated acidsCu(NO₃)₂(E)-Nitroolefins

Electronic supplementary material

The online version of this article (doi:10.1007/s11164-016-2446-6) contains supplementary material, which is available to authorized users.

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Supplementary material

11164_2016_2446_MOESM1_ESM.doc (2.3 mb)

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References

1. 1.
   M.A. Reddy, N. Jain, D. Yada, C. Kishore, V.J. Reddy, P.S. Reddy, A. Addlagatta, S.V. Kalivendi, B. Sreedhar, J. Med. Chem. 54, 6751 (2011)CrossRefGoogle Scholar
2. 2.
   L.Q. Lu, J.R. Chen, W.J. Xiao, Acc. Chem. Res. 45, 1278 (2012)CrossRefGoogle Scholar
3. 3.
   C.B. Tripathi, S. Kayal, S. Mukherjee, Org. Lett. 14, 3296 (2012)CrossRefGoogle Scholar
4. 4.
   Y.K. Liu, M. Nappi, E. Arceo, S. Vera, P. Melchiorre, J. Am. Chem. Soc. 133, 15212 (2011)CrossRefGoogle Scholar
5. 5.
   D.K. Nair, S.M. Mobin, I.N.N. Namboothiri, Org. Lett. 14, 4580 (2012)CrossRefGoogle Scholar
6. 6.
   R. Tamura, A. Kamimura, N. Ono, Synthesis 6, 423 (1991)CrossRefGoogle Scholar
7. 7.
   S. Fioravanti, L. Pellacani, P.A. Tardella, M.C. Vergari, Org. Lett. 10, 1449 (2008)CrossRefGoogle Scholar
8. 8.
   S. Maity, S. Manna, S. Rana, T. Naveen, A. Mallick, D. Maiti, J. Am. Chem. Soc. 135, 3355 (2013)CrossRefGoogle Scholar
9. 9.
   T. Naveen, S. Maity, U. Sharma, D. Maiti, J. Org. Chem. 78, 5949 (2013)CrossRefGoogle Scholar
10. 10.
    S. Maity, T. Naveen, U. Sharma, D. Maiti, Org. Lett. 15, 3384 (2013)CrossRefGoogle Scholar
11. 11.
    U. Dutta, S. Maity, R. Kancherla, D. Maiti, Org. Lett. 16, 6302 (2014)CrossRefGoogle Scholar
12. 12.
    G.B. Yan, A.J. Borah, L.G. Wang, Org. Biomol. Chem. 12, 6049 (2014)CrossRefGoogle Scholar
13. 13.
    P. Natarajan, R. Chaudhary, P. Venugopalan, J. Org. Chem. 80, 10498 (2015)CrossRefGoogle Scholar
14. 14.
    A.J. Borah, G.B. Yan, Org. Biomol. Chem. 13, 8094 (2015)CrossRefGoogle Scholar
15. 15.
    J.P. Das, P. Sinha, S. Roy, Org. Lett. 4, 3055 (2002)CrossRefGoogle Scholar
16. 16.
    A.S. Rao, P.V. Srinivas, K.S. Babu, J.M. Rao, Tetrahedron Lett. 46, 8141 (2005)CrossRefGoogle Scholar
17. 17.
    K.C. Rajanna, K. Ramesh, S. Ramgopal, S. Shylaja, P.G. Reddy, P.K. Saiprakash, Green Sustain. Chem. 1, 132 (2011)CrossRefGoogle Scholar
18. 18.
    S. Manna, S. Jana, T. Saboo, A. Maji, D. Maiti, Chem. Commun. 49, 5286 (2013)CrossRefGoogle Scholar
19. 19.
    B.V. Rokade, K.R. Prabhu, Org. Biomol. Chem. 11, 6713 (2013)CrossRefGoogle Scholar
20. 20.
    Diganta. Baruah, Pallab. Pahari, Dilip. Konwar, Tetrahedron Lett. 56, 2418 (2015)CrossRefGoogle Scholar
21. 21.
    M. Zhang, P. Hu, J. Zhou, G. Wu, W.P. Su, Org. Lett. 15, 1718 (2013)CrossRefGoogle Scholar

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© Springer Science+Business Media Dordrecht 2016