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Abstract
Nicotine-based task specific ionic liquid has been used as a carrier of boron hydride instead of pyridine borane and other related reagents. Borohydride complex of nicotine-ionic liquid (IL) has been used for reductive amination of variety of carbonyls and amines with encouraging results. The reactions were conducted under pyridine free odourless conditions. The improved results were obtained in terms of enhanced yields, with minimal work up.
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References
- S.H. Bauer, Chem. Rev., 31, 43 (1942); https://doi.org/10.1021/cr60098a002.
- N.M. Yoon, C.S. Pak, S. Krishnamurthy, T.P. Stocky and H.C. Brown, J. Org. Chem., 38, 2786 (1973); https://doi.org/10.1021/jo00956a011.
- H. Jockel and R. Schmidt, J. Chem. Soc. Perkin Trans. II, 2719 (1997); https://doi.org/10.1039/a703698a.
- J.C. Amedio, P.J. Bernard, M. Fountain and G.V. Wagenen, Synth. Commun., 29, 2377 (1999); https://doi.org/10.1080/00397919908086243.
- R.O. Hutchins, K. Learn, B. Nazer, D. Pytlewski and A. Pelter, Org. Prep. Proced. Int., 16, 335 (1984); https://doi.org/10.1080/00304948409457891.
- B. Carboni and L. Monnier, Tetrahedron, 55, 1197 (1999); https://doi.org/10.1016/S0040-4020(98)01103-X.
- A. Volkov, F. Tinnis, T. Slagbrand, P. Trilloa and H. Adolfsson, Chem. Soc. Rev., 45, 6685 (2016); https://doi.org/10.1039/C6CS00244G.
- A. Pelter, R.M. Rosser and S. Mills, J. Chem. Soc., Perkin Trans. 1, 4, 717 (1984); https://doi.org/10.1039/P19840000717.
- (a) P.G.M. Wuts, J.E. Cabaj and J.L. Havens, J. Org. Chem., 59, 6470 (1994); https://doi.org/10.1021/jo00100a061. (b) T. Sakamoto, H. Li and Y. Kikugawa, J. Org. Chem., 61, 8496 (1996); https://doi.org/10.1021/jo961458f.
- R.P. Tripathi, S.S. Verma, J. Pandey and V.K. Tiwari, Curr. Org. Chem., 12, 1093 (2008); https://doi.org/10.2174/138527208785740283.
- A.E. Moormann, Synth. Commun., 23, 789 (1993); https://doi.org/10.1080/00397919308009840.
- M.D. Bomann, I.C. Guch and M. DiMare, J. Org. Chem., 60, 5995 (1995); https://doi.org/10.1021/jo00123a049.
- S. Sato, T. Sakamoto, E. Miyazawa and Y. Kikugawa, Tetrahedron, 60, 7899 (2004); https://doi.org/10.1016/j.tet.2004.06.045.
- A.A. Hullio and G.M. Mastoi, Oriental J. Chem., 27, 1591 (2011).
- A.A. Hullio and G.M. Mastoi, Asian J. Chem., 23, 5411 (2011).
- A.A. Hullio and G.M. Mastoi, Chin. J. Chem., 30, 1647 (2012); https://doi.org/10.1002/cjoc.201280028.
- A.A. Hullio and G.M. Mastoi, Iranian J. Catal., 1, 79 (2011).
- E. Ennis and S. Handy, Curr. Org. Synth., 4, 381 (2007); https://doi.org/10.2174/157017907782408824.
- AA. Hullio and G.M. Mastoi, Jordan J. Chem, 7, 125 (2012).
- S.T. Handy, M. Okello and G. Dickenson, Org. Lett., 5, 2513 (2003); https://doi.org/10.1021/ol034778b.
- M. Shibagaki, H. Matsushta and H. Kaneko, Heterocycles, 20, 497 (1983); https://doi.org/10.3987/R-1983-03-0497.
References
S.H. Bauer, Chem. Rev., 31, 43 (1942); https://doi.org/10.1021/cr60098a002.
N.M. Yoon, C.S. Pak, S. Krishnamurthy, T.P. Stocky and H.C. Brown, J. Org. Chem., 38, 2786 (1973); https://doi.org/10.1021/jo00956a011.
H. Jockel and R. Schmidt, J. Chem. Soc. Perkin Trans. II, 2719 (1997); https://doi.org/10.1039/a703698a.
J.C. Amedio, P.J. Bernard, M. Fountain and G.V. Wagenen, Synth. Commun., 29, 2377 (1999); https://doi.org/10.1080/00397919908086243.
R.O. Hutchins, K. Learn, B. Nazer, D. Pytlewski and A. Pelter, Org. Prep. Proced. Int., 16, 335 (1984); https://doi.org/10.1080/00304948409457891.
B. Carboni and L. Monnier, Tetrahedron, 55, 1197 (1999); https://doi.org/10.1016/S0040-4020(98)01103-X.
A. Volkov, F. Tinnis, T. Slagbrand, P. Trilloa and H. Adolfsson, Chem. Soc. Rev., 45, 6685 (2016); https://doi.org/10.1039/C6CS00244G.
A. Pelter, R.M. Rosser and S. Mills, J. Chem. Soc., Perkin Trans. 1, 4, 717 (1984); https://doi.org/10.1039/P19840000717.
(a) P.G.M. Wuts, J.E. Cabaj and J.L. Havens, J. Org. Chem., 59, 6470 (1994); https://doi.org/10.1021/jo00100a061. (b) T. Sakamoto, H. Li and Y. Kikugawa, J. Org. Chem., 61, 8496 (1996); https://doi.org/10.1021/jo961458f.
R.P. Tripathi, S.S. Verma, J. Pandey and V.K. Tiwari, Curr. Org. Chem., 12, 1093 (2008); https://doi.org/10.2174/138527208785740283.
A.E. Moormann, Synth. Commun., 23, 789 (1993); https://doi.org/10.1080/00397919308009840.
M.D. Bomann, I.C. Guch and M. DiMare, J. Org. Chem., 60, 5995 (1995); https://doi.org/10.1021/jo00123a049.
S. Sato, T. Sakamoto, E. Miyazawa and Y. Kikugawa, Tetrahedron, 60, 7899 (2004); https://doi.org/10.1016/j.tet.2004.06.045.
A.A. Hullio and G.M. Mastoi, Oriental J. Chem., 27, 1591 (2011).
A.A. Hullio and G.M. Mastoi, Asian J. Chem., 23, 5411 (2011).
A.A. Hullio and G.M. Mastoi, Chin. J. Chem., 30, 1647 (2012); https://doi.org/10.1002/cjoc.201280028.
A.A. Hullio and G.M. Mastoi, Iranian J. Catal., 1, 79 (2011).
E. Ennis and S. Handy, Curr. Org. Synth., 4, 381 (2007); https://doi.org/10.2174/157017907782408824.
AA. Hullio and G.M. Mastoi, Jordan J. Chem, 7, 125 (2012).
S.T. Handy, M. Okello and G. Dickenson, Org. Lett., 5, 2513 (2003); https://doi.org/10.1021/ol034778b.
M. Shibagaki, H. Matsushta and H. Kaneko, Heterocycles, 20, 497 (1983); https://doi.org/10.3987/R-1983-03-0497.