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Solvent-Free Alkylation of 1,3-Dicarbonyl Compounds with Benzylic, Propargylic and Allylic Alcohols Catalyzed by La(NO3)3·6H2O
Corresponding Author(s) : Koya Prabhakara Rao
Asian Journal of Chemistry,
Vol. 28 No. 5 (2016): Vol 28 Issue 5
Abstract
An efficient and solvent free method for benzylation, propargylation and allylation of 1,3-dicarbonyl compounds with alcohols has been developed by using La(NO3)3·6H2O as water tolerable catalyst. The reaction was shown to proceed smoothly for various 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols including 10 allylic alcohols, without any solvent, providing a clean access to the desired products in short reaction times with good to excellent yields and high selectivity.
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References
J. March, Advanced Organic Chemistry, Wiley, New York, edn 4 (1992).
C. Scolastic and F. Nocotra, Current Trends in Organic Synthesis, Plenum: New York (1999).
J. Kischel, K. Mertins, D. Michalik, A. Zapf and M. Beller, Adv. Synth. Catal., 349, 865 (2007); doi:10.1002/adsc.200600497.
V. Narayana, R. Varala and P. Zubaidha, Int. J. Org. Chem., 02, 287 (2012); doi:10.4236/ijoc.2012.223039.
B.A. Keay and P.W. Dibble, in eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry II; Elsevier: Oxford, vol. 2, p. 395 (1997).
R.C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, VCH: New York, edn 2 (1999).
S. Arumugam, D. McLeod and J.G. Verkade, J. Org. Chem., 63, 3677 (1998); doi:10.1021/jo972350i.
M. Moreno-Manas, J. Marquet and A. Vallribera, Tetrahedron, 52, 3377 (1996); doi:10.1016/0040-4020(95)01020-3.
B.M. Trost, Science, 254, 1471 (1991); doi:10.1126/science.1962206.
R.A. Sheldon, Chemtech., 38 (1994).
R.A. Sheldon, Pure Appl. Chem., 72, 1233 (2000); doi:10.1351/pac200072071233.
K. Manabe and S. Kobayashi, Org. Lett., 5, 3241 (2003); doi:10.1021/ol035126q.
M. Mukhopadhyay and J. Iqbal, Tetrahedron Lett., 36, 6761 (1995); doi:10.1016/0040-4039(95)01335-F.
F. Bisaro, G. Prestat, M. Vitale and G. Poli, Synlett, 1823 (2002); doi:10.1055/s-2002-34884.
M. Yasuda, T. Somyo and A. Baba, Angew. Chem. Int., 45, 793 (2006); doi:10.1002/anie.200503263.
M. Rueping, B.J. Nachtsheim and A. Kuenkel, Org. Lett., 9, 825 (2007); doi:10.1021/ol063048b.
W. Huang, J. Wang, Q. Shen and X. Zhou, Tetrahedron Lett., 48, 3969 (2007); doi:10.1016/j.tetlet.2007.04.047.
U. Jana, S. Biswas and S. Maiti, Tetrahedron Lett., 48, 4065 (2007); doi:10.1016/j.tetlet.2007.04.017.
K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani and K. Kaneda, Angew. Chem. Int. Ed., 45, 2605 (2006); doi:10.1002/anie.200504609.
M. Noji, Y. Konno and K. Ishii, J. Org. Chem., 72, 5161 (2007); doi:10.1021/jo0705216.
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P.N. Liu, L. Dang, Q.W. Wang, S.L. Zhao, F. Xia, Y.J. Ren, X.Q. Gong and J.Q. Chen, J. Org. Chem., 75, 5017 (2010); doi:10.1021/jo100517k.
J.B. Baruah and A.G. Samuelson, J. Organomet. Chem., 361, C57 (1989); doi:10.1016/0022-328X(89)87015-9.
P.N. Chatterjee and S. Roy, Tetrahedron, 67, 4569 (2011); doi:10.1016/j.tet.2011.04.092.
P. Kothandaraman, W. Rao, X. Zhang and P.W.H. Chan, Tetrahedron, 65, 1833 (2009); doi:10.1016/j.tet.2008.11.102.
J.S. Yadav, B.V. Subba Reddy, T. Pandurangam, K.V. Raghavendra Rao, K. Praneeth, G.G.K.S. Narayana Kumar, C. Madavi and A.C. Kunwar, Tetrahedron Lett., 49, 4296 (2008); doi:10.1016/j.tetlet.2008.04.126.
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.
A. Loupy, Top. Curr. Chem., 206, 153 (1999); doi:10.1007/3-540-48664-X_7.
G.W.V. Cave, J.C. Raston and L. Scott, Chem. Commun., 2159 (2001); doi:10.1039/b106677n.
J.O. Metzger, in eds.: H.-G. Schmalz and T. Wirth, Organic Synthesis Highlights V, Wiley-VCH: Weinheim (2003).
T.S. Reddy, M. Narasimhulu, N. Suryakiran, K.C. Mahesh, K. Ashalatha and Y. Venkateswarlu, Tetrahedron Lett., 47, 6825 (2006); doi:10.1016/j.tetlet.2006.07.059.
M.R. Mousavi, J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani and M. Safarzaei, Lett. Org. Chem., 10, 171 (2013); doi:10.2174/1570178611310030005.
V. Venkata Rami Reddy, A. Tejaswara Rao, A. Jayashree and R. Varala, Der. Pharma Chem., 6, 73 (2014).
V. Venkata Rami Reddy, B. Saritha, R. Ramu, R. Varala and A. Jayashree, Asian J. Chem., 26, 7439 (2014); doi:10.14233/ajchem.2014.17180.
A. Kasa, R. Varala, P.M. Swami and P.K. Zubaidha, Chem. J., 3, 66 (2013).
V.R. Narayana, Z. Pudukulathan and R. Varala, Org. Commun., 6, 110 (2013).
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