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Ultrasound Assisted Nitratobis(triphenyl phosphine) Copper(I) Catalyzed Conjugate Addition of Alkyl or Aryl Bromides to α,β-Unsaturated Cyanoester
Corresponding Author(s) : Ashok S. Pise
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
The α,β-unsaturated cyanoester was obtained from p-methoxy benzaldehyde and ethyl cyano acetate by reported method. The conjugated addition products were synthesized from alkyl or aryl bromides and α,β-unsaturated cyanoester in the presence of 10 mol % Cu(I) catalyst in high yields within 17-21 min under ultrasound irradiation.
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- W. Richards and A. Loomis, J. Am. Chem. Soc., 49, 3086 (1927); https://doi.org/10.1021/ja01411a015.
- L.A. Sarandeses, A. Mouriño and J.L. Luche, J. Chem. Soc. Chem. Commun., 798 (1992); https://doi.org/10.1039/C39920000798.
- C. Dupuy, C. Petrier, L.A. Sarandeses and J.L. Luche, Synth. Commun., 21, 643 (1991); https://doi.org/10.1080/00397919108020831.
- T.J. Mason, Practical Sonochemistry, Ellis Howood Limited: New York (1991).
- W.J. Houlihan, Indoles, John Wiley & Sons Inc.: New York (1972).
- P. Knochel, Hand book of Functionlized Organometallics, Wiely VCH, vol. 1, Chap. 7 (2005).
- P. Knochel, J.J. Almena Perea and P. Jones, Tetrahedron, 54, 8275 (1998); https://doi.org/10.1016/S0040-4020(98)00318-4.
- E. Negishi, Organometallics in Organic Synthesis, Wiely: New York, vol. 1 (1980).
- I. Antes and G. Frenking, Organometallics, 14, 4263 (1995); https://doi.org/10.1021/om00009a032.
- R.D. Rieke, Substituted Polythiophenes from Highly Reactive Zinc Reagents, US Patent 00576653A (1998).
- B.H. Lipshutz, P.A. Blomgren and S.K. Kim, Tetrahedron Lett., 40, 197 (1999); https://doi.org/10.1016/S0040-4039(98)02271-0.
- C. Dai and G.C. Fu, J. Am. Chem. Soc., 123, 2719 (2001); https://doi.org/10.1021/ja003954y.
- B.H. Lipshutz and S. Sengupta, Org. React., 41, 135 (1992); https://doi.org/10.1002/0471264180.or041.02.
- M.B. Deshmukh, S.D. Jadhav, A.R. Mali, A.W. Suryawanshi, P.V. Anbhule, S.S. Jagtap and S.A. Deshmukh, Synth. Commun., 35, 2967 (2005); https://doi.org/10.1080/00397910500278461.
- J.-T. Li, Indian J. Chem., 47B, 283 (2008).
- D. Kanwar, R. Rani, J. Agarwal and R.K. Peddinti, Indian J. Chem., 49B, 1290 (2010).
- V. Kumar, S. Kaur and S. Kumar, Tetrahedron Lett., 47, 7001 (2006); https://doi.org/10.1016/j.tetlet.2006.07.116.
- P. Arumugam and P.T. Perumal, Chem. Lett., 35, 632 (2006); https://doi.org/10.1246/cl.2006.632.
- A. Arcadi, G. Bianchi, M. Chiarini, G. D’Anniballe and F. Marinelli, Synlett, 944 (2004); https://doi.org/10.1055/s-2004-822903.
- G. Bartoli, M. Bartolacci, M. Bosco, A. Giuliani, E. Marcantoni, G. Foglia, L. Sambri and E. Torregiani, J. Org. Chem., 68, 4594 (2003); https://doi.org/10.1021/jo034303y.
- S.E. Denmark and N. Amishiro, J. Org. Chem., 68, 6997 (2003); https://doi.org/10.1021/jo034763r.
- M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva and A. Umani-Ronchi, J. Org. Chem., 67, 3700 (2002); https://doi.org/10.1021/jo0163243.
- Z.H. Huang, J.P. Zou and W.Q. Jiang, Tetrahedron Lett., 47, 7965 (2006); https://doi.org/10.1016/j.tetlet.2006.08.108.
- M.B. Andrus, Z. Ye and J. Zhang, Tetrahedron Lett., 46, 3839 (2005); https://doi.org/10.1016/j.tetlet.2005.03.185.
- Z. Li, Z. Shi and C. He, Organomet. Chem., 690, 5049 (2005); https://doi.org/10.1016/j.jorganchem.2005.03.009.
- J.S. Yadav, B.V.S. Reddy, G. Baishya, K.V. Reddy and A.V. Narsaiah, Tetrahedron Lett., 61, 9541 (2005); https://doi.org/10.1016/j.tet.2005.07.095.
- C.A.M.A. Huq and A.R. Naresh Raj, Indian J. Chem., 42B, 1451 (2013).
- S. Kotha and R. Ali, Indian J. Chem., 55B, 1099 (2016).
- E. Korkusuz and I. Yildirim, Indian J. Chem., 56B, 152 (2017).
- D. Bandyopadhyay, S. Mukherjee, L. Turrubiartes and B.K. Banik, Ultrason. Sonochem., 19, 969 (2012); https://doi.org/10.1016/j.ultsonch.2011.11.009.
- A.S. Pise, A.S. Burungale, R.B. Gawade and S.D. Jadhav, Int. J. Sci. Res. Sci. Technol., 2, 446 (2018).
References
W. Richards and A. Loomis, J. Am. Chem. Soc., 49, 3086 (1927); https://doi.org/10.1021/ja01411a015.
L.A. Sarandeses, A. Mouriño and J.L. Luche, J. Chem. Soc. Chem. Commun., 798 (1992); https://doi.org/10.1039/C39920000798.
C. Dupuy, C. Petrier, L.A. Sarandeses and J.L. Luche, Synth. Commun., 21, 643 (1991); https://doi.org/10.1080/00397919108020831.
T.J. Mason, Practical Sonochemistry, Ellis Howood Limited: New York (1991).
W.J. Houlihan, Indoles, John Wiley & Sons Inc.: New York (1972).
P. Knochel, Hand book of Functionlized Organometallics, Wiely VCH, vol. 1, Chap. 7 (2005).
P. Knochel, J.J. Almena Perea and P. Jones, Tetrahedron, 54, 8275 (1998); https://doi.org/10.1016/S0040-4020(98)00318-4.
E. Negishi, Organometallics in Organic Synthesis, Wiely: New York, vol. 1 (1980).
I. Antes and G. Frenking, Organometallics, 14, 4263 (1995); https://doi.org/10.1021/om00009a032.
R.D. Rieke, Substituted Polythiophenes from Highly Reactive Zinc Reagents, US Patent 00576653A (1998).
B.H. Lipshutz, P.A. Blomgren and S.K. Kim, Tetrahedron Lett., 40, 197 (1999); https://doi.org/10.1016/S0040-4039(98)02271-0.
C. Dai and G.C. Fu, J. Am. Chem. Soc., 123, 2719 (2001); https://doi.org/10.1021/ja003954y.
B.H. Lipshutz and S. Sengupta, Org. React., 41, 135 (1992); https://doi.org/10.1002/0471264180.or041.02.
M.B. Deshmukh, S.D. Jadhav, A.R. Mali, A.W. Suryawanshi, P.V. Anbhule, S.S. Jagtap and S.A. Deshmukh, Synth. Commun., 35, 2967 (2005); https://doi.org/10.1080/00397910500278461.
J.-T. Li, Indian J. Chem., 47B, 283 (2008).
D. Kanwar, R. Rani, J. Agarwal and R.K. Peddinti, Indian J. Chem., 49B, 1290 (2010).
V. Kumar, S. Kaur and S. Kumar, Tetrahedron Lett., 47, 7001 (2006); https://doi.org/10.1016/j.tetlet.2006.07.116.
P. Arumugam and P.T. Perumal, Chem. Lett., 35, 632 (2006); https://doi.org/10.1246/cl.2006.632.
A. Arcadi, G. Bianchi, M. Chiarini, G. D’Anniballe and F. Marinelli, Synlett, 944 (2004); https://doi.org/10.1055/s-2004-822903.
G. Bartoli, M. Bartolacci, M. Bosco, A. Giuliani, E. Marcantoni, G. Foglia, L. Sambri and E. Torregiani, J. Org. Chem., 68, 4594 (2003); https://doi.org/10.1021/jo034303y.
S.E. Denmark and N. Amishiro, J. Org. Chem., 68, 6997 (2003); https://doi.org/10.1021/jo034763r.
M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva and A. Umani-Ronchi, J. Org. Chem., 67, 3700 (2002); https://doi.org/10.1021/jo0163243.
Z.H. Huang, J.P. Zou and W.Q. Jiang, Tetrahedron Lett., 47, 7965 (2006); https://doi.org/10.1016/j.tetlet.2006.08.108.
M.B. Andrus, Z. Ye and J. Zhang, Tetrahedron Lett., 46, 3839 (2005); https://doi.org/10.1016/j.tetlet.2005.03.185.
Z. Li, Z. Shi and C. He, Organomet. Chem., 690, 5049 (2005); https://doi.org/10.1016/j.jorganchem.2005.03.009.
J.S. Yadav, B.V.S. Reddy, G. Baishya, K.V. Reddy and A.V. Narsaiah, Tetrahedron Lett., 61, 9541 (2005); https://doi.org/10.1016/j.tet.2005.07.095.
C.A.M.A. Huq and A.R. Naresh Raj, Indian J. Chem., 42B, 1451 (2013).
S. Kotha and R. Ali, Indian J. Chem., 55B, 1099 (2016).
E. Korkusuz and I. Yildirim, Indian J. Chem., 56B, 152 (2017).
D. Bandyopadhyay, S. Mukherjee, L. Turrubiartes and B.K. Banik, Ultrason. Sonochem., 19, 969 (2012); https://doi.org/10.1016/j.ultsonch.2011.11.009.
A.S. Pise, A.S. Burungale, R.B. Gawade and S.D. Jadhav, Int. J. Sci. Res. Sci. Technol., 2, 446 (2018).