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CuSCN Catalyzed Conjugate Addition of Grignard Reagents to Substituted Coumarins with Dilithium Tetrachloromanganate
Corresponding Author(s) : Shrikant B. Jagtap
Asian Journal of Chemistry,
Vol. 32 No. 7 (2020): Vol 32 Issue 7
Abstract
The regioselective 1,4-addition of CuSCN catalyzed Grignard reagents to the substituted coumarins are reported. The Li2MnCl4 reagent is used to transmetallate magnesium by manganese. It adds regioselectively to coumarins and forms 1,4-addition products with higher yield under the atmosphere of nitrogen gas and at a lower temperature.
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- A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221 (2002); https://doi.org/10.1002/1099-0690(200210)2002:19<3221::AIDEJOC3221>3.0.CO;2-U
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- B.L. Feringa, Acc. Chem. Res., 33, 346 (2000); https://doi.org/10.1021/ar990084k
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- Z. Ma, F. Xie, H. Yu, Y. Zhang, X. Wu and W. Zhang, Chem. Commun., 49, 5292 (2013); https://doi.org/10.1039/C3CC42088D
- G.S. Silverman and P.E. Rakita, Handbook of Grignard Reagents, Dekker; CRC Press: New York, NY, USA (1996).
- T. Hoim and I. Crossland, ed.: H.G. Richey Jr., Mechanistic Featuresof the Reactions of Organomagnesium Compounds, In: Grignard ReagentsNew Devlopments, John Wiley & Sons: Chichster, UK (2000).
- T. Laird, eds.: D. Barton, W.D. Ollis and J.F. Stoddard, Aromatic Ketones in Comprehensive Organic Chemistry, Pergamon Press: Oxford, UK; volume 1, Chap. 5.4; pp. 1174-1181 (1979).
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- F. Wessely and J. Kotlan, Monatsh. Chem., 84, 124 (1953); https://doi.org/10.1007/BF00899130
- B. Miller, J. Org. Chem., 42, 1402 (1977); https://doi.org/10.1021/jo00428a030
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- D. Wege, Aust. J. Chem., 24, 1531 (1971); https://doi.org/10.1071/CH9711531
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- C. Boga, L. Forlani and P.E. Todesco, Gazz. Chim. Ital., 127, 197 (1997).
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- T. Jerphagnon, G. Pizzuti, A.J. Minnaard and B.L. Feringa, Chem. Soc. Rev., 38, 1039 (2009); https://doi.org/10.1039/B816853A
References
A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221 (2002); https://doi.org/10.1002/1099-0690(200210)2002:19<3221::AIDEJOC3221>3.0.CO;2-U
S. Woodward, Angew. Chem. Int. Ed., 44, 5560 (2005); https://doi.org/10.1002/anie.200501204
G.M. Villacorta, C.P. Rao and S.J. Lippard, J. Am. Chem. Soc., 110, 3175 (1988); https://doi.org/10.1021/ja00218a028
B.L. Feringa, R. Badorrey, D. Pena, S.R. Harutyunyan and A.J. Minnaard, J. Proc. Natl. Acad. Sci. USA, 101, 5834 (2004); https://doi.org/10.1073/pnas.0308008101
T. Jerphagnon, M.G. Pizzuti, A.J. Minnaard and B.L. Feringa, Chem. Soc. Rev., 38, 1039 (2009); https://doi.org/10.1039/b816853a
D. Martin, S. Kehrli, M. d’Augustin, H. Clavier, M. Mauduit and A. Alexakis, J. Am. Chem. Soc., 128, 8416 (2006); https://doi.org/10.1021/ja0629920
A. Alexakis, J.E. Bäckvall, N. Krause, O. Pàmies and M. Diéguez, Chem. Rev., 108, 2796 (2008); https://doi.org/10.1021/cr0683515
F. Lopez, S.R. Harutyunyan, A. Meetsma, A.J. Minnaa Rd and B.L. Feringa, Angew. Chem. Int. Ed., 44, 2752 (2005); https://doi.org/10.1002/anie.200500317
R.D. Mazery, M. Pullez F. Lopez, S.R. Harutyunyan, A.J. Minnaard and B.L. Feringa, J. Am. Chem. Soc., 127, 9966 (2005); https://doi.org/10.1021/ja053020f
T.E. Schmid, S. Drissi-Amraoui, C. Crévisy, O. Baslé and M. Mauduit, Beilstein J. Org. Chem., 11, 2418 (2015); https://doi.org/10.3762/bjoc.11.263
J.F. Teichert and B.L. Feringa, Angew. Chem. Int. Ed., 49, 2486 (2010); https://doi.org/10.1002/anie.200904948
B.L. Feringa, M. Pineschi, L.A. Arnold, R. Imbos and A.H.M. de Vries, Angew. Chem. Int. Ed. Engl., 36, 2620 (1997); https://doi.org/10.1002/anie.199726201
J.N. Moorthy, P. Venkatakrishnan, S. Sengupta and M. Baidya, Org. Lett., 8, 4891 (2006); https://doi.org/10.1021/ol0619260
K. Afarinkia, V. Vinader, T.D. Nelson and G.H. Posner, Tetrahedron, 48, 9111 (1992); https://doi.org/10.1016/S0040-4020(01)85607-6
B.L. Feringa, Acc. Chem. Res., 33, 346 (2000); https://doi.org/10.1021/ar990084k
K.C. Nicolaou, J.J. Liu, C.-K. Hwang, W.-M. Dai and R.K. Guy, J. Chem. Soc. Chem. Commun., 1118 (1992); https://doi.org/10.1039/c39920001118
A.G. Csákÿ, G. Herrán and M.C. Murcia, Chem. Soc. Rev., 39, 4080 (2010); https://doi.org/10.1039/b924486g
F. Lopez, S.R. Harutyunyan, A.J. Minnaard and B.L. Feringa, J. Am. Chem. Soc., 126, 12784 (2004); https://doi.org/10.1021/ja046632t
Z. Ma, F. Xie, H. Yu, Y. Zhang, X. Wu and W. Zhang, Chem. Commun., 49, 5292 (2013); https://doi.org/10.1039/C3CC42088D
G.S. Silverman and P.E. Rakita, Handbook of Grignard Reagents, Dekker; CRC Press: New York, NY, USA (1996).
T. Hoim and I. Crossland, ed.: H.G. Richey Jr., Mechanistic Featuresof the Reactions of Organomagnesium Compounds, In: Grignard ReagentsNew Devlopments, John Wiley & Sons: Chichster, UK (2000).
T. Laird, eds.: D. Barton, W.D. Ollis and J.F. Stoddard, Aromatic Ketones in Comprehensive Organic Chemistry, Pergamon Press: Oxford, UK; volume 1, Chap. 5.4; pp. 1174-1181 (1979).
C. Blomberg, H.H. Grootveld, T.H. Gerner and F. Bickelhaupt, J. Organomet. Chem., 24, 549 (1970); https://doi.org/10.1016/S0022-328X(00)84483-6
F. Wessely and J. Kotlan, Monatsh. Chem., 84, 124 (1953); https://doi.org/10.1007/BF00899130
B. Miller, J. Org. Chem., 42, 1402 (1977); https://doi.org/10.1021/jo00428a030
B. Miller, J. Org. Chem., 42, 1408 (1977); https://doi.org/10.1021/jo00428a031
D. Wege, Aust. J. Chem., 24, 1531 (1971); https://doi.org/10.1071/CH9711531
T. Holm, R. Stomberg, S. von Unge and A.-B. Wassgren, Acta Chem. Scand. Ser. B, 41, 278 (1987); https://doi.org/10.3891/acta.chem.scand.41b-0278
C. Boga, L. Forlani and P.E. Todesco, Tetrahedron Lett., 38, 4845 (1997); https://doi.org/10.1016/S0040-4039(97)01009-5
C. Boga, L. Forlani and P.E. Todesco, Gazz. Chim. Ital., 127, 197 (1997).
C. Boga, R. Stengel, R. Abdayem, E. Del Vecchio, L. Forlani and P.E.Todesco, J. Org. Chem., 69, 8903 (2004); https://doi.org/10.1021/jo048948p
B.F. Abdel-Wahab, H.A. Mohamed and A.A. Farhat, Org. Commun., 7, 1 (2014).
T. Jerphagnon, G. Pizzuti, A.J. Minnaard and B.L. Feringa, Chem. Soc. Rev., 38, 1039 (2009); https://doi.org/10.1039/B816853A