M. Dixit et al. / Catalysis Communications 33 (2013) 80–83
83
[13] C.S. Cho, B.T. Kim, T.-J. Kim, S.C. Shim, Tetrahedron Letters 43 (2002) 7987–7989.
[14] K. Taguchi, H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, Journal of the
American Chemical Society 126 (2004) 72–73.
[15] R. Martinez, G.J. Brand, D.J. Ramon, M. Yus, Tetrahedron Letters 46 (2005) 3683–3686.
[16] P.J. Black, G. Cami-Kobeci, M.G. Edwards, P.A. Slatford, M.K. Whittlesey, J.M.J. Williams,
Organic and Biomolecular Chemistry 4 (2006) 116–125.
[17] R. Martinez, G.J. Brand, D.J. Ramon, M. Yus, Tetrahedron Letters 62 (2006) 8988–9001.
[18] C.S. Cho, Catalysis Communications 7 (2006) 1012–1014.
[19] P.A. Slatford, M.K. Whittlesey, J.M.J. Williams, Tetrahedron Letters 47 (2006)
6787–6789.
support basicity, etc.) can also be tuned to have enhanced activity for
these reactions. The high activity of Cu-HT for borrowing hydrogen is
evident from its capability to activate the primary, secondary and ben-
zylic alcohols for reaction with deactivated substrates (acetophenone
and aniline).
4. Conclusion
[20] M. Morita, Y. Obora, Y. Ishii, Chemical Communications (2007) 2850–2852.
[21] S. Liao, K. Yu, Q. Li, H. Tian, Z. Zhang, X. Yu, Q. Xu, Organic and Biomolecular
Chemistry 10 (2012) 2973–2978.
[22] R. Grigg, T.R.B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, Journal of the Chemical
Society, Chemical Communications 12 (1981) 611–612.
The Cu-HT has great potential for catalysis of C- and N-alkylation re-
actions using alcohols as alkylating agent via borrowing hydrogen
route, which can provide a very clean (solvent free, base free, ligands
free and without hydrogen acceptor) process for synthesis of alkylated
ketones and amines. The scope of Cu-HT could be as an efficient and
cheap catalyst for α-alkylation of ketones, β-alkylation of alcohols, al-
kylation of amines and amides by borrowing hydrogen methodology.
[23] K.-I. Fujita, R. Yamaguchi, Synlett 4 (2005) 560–571.
[24] G. Cami-Kobeci, P.A. Slatford, M.K. Whittlesey, J.M.J. Williams, Bioorganic
&
Medicinal Chemistry Letters 15 (2005) 535–537.
[25] B. Blank, M. Madalska, R. Kempe, Advanced Synthesis and Catalysis 350 (2008)
749–758.
[26] A. Tillack, D. Hollmann, D. Michalik, M. Beller, Tetrahedron Letters 47 (2006)
8881–8885.
[27] D. Hollmann, A. Tillack, D. Michalik, R. Jackstell, M. Beller, Chemistry, an Asian
Journal 2 (2007) 403–410.
Acknowledgments
Authors are thankful to Dr. H.M. Desai, Vice-Chancellor DDU &
GUJCOST for necessary support.
[28] M.H.S.A. Hamid, J.M.J. Williams, Chemical Communications (Cambridge, England)
7 (2007) 725–727.
[29] A. Prades, R. Corberán, M. Poyatos, E. Peris, Chemistry 14 (2008) 11474–11479.
[30] B. Blank, S. Michlik, R. Kempe, Chemistry 15 (2009) 3790–3799.
[31] O. Saidi, A.J. Blacker, M.M. Farah, S.P. Marsden, J.M.J. Williams, Chemical Commu-
nications (Cambridge, England) 46 (2010) 1541–1543.
Appendix A. Supplementary data
[32] Q. Li, S. Fan, Q. Sun, H. Tian, X. Yu, Q. Xu, Organic and Biomolecular Chemistry 10
(2012) 2966–2972.
Supplementary data to this article can be found online at http://
[33] K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Journal of
the American Chemical Society 126 (2004) 5662–5663.
[34] C.S. Cho, Journal of Molecular Catalysis A: Chemical 240 (2005) 55–60.
[35] M.S. Kwon, N. Kim, S.H. Seo, I.S. Park, R.K. Cheedrala, J. Park, Angewandte Chemie
International Edition 44 (2005) 6913–6915.
[36] Y.M.A. Yamada, Y. Uozumi, Organic Letters 8 (2006) 1375–1378.
[37] K. Kaneda, T. Mitsudome, T. Mizugaki, K. Jitsukawa, Molecules 15 (2010) 8988–9007.
[38] Y. Perez, R. Ballesteros, M. Fajardo, I. Sierra, I. del Hierro, Journal of Molecular
Catalysis A: Chemical 352 (2012) 45–56.
[39] K.V.R. Chary, K.K. Seela, D. Naresh, P. Ramakanth, Catalysis Communications 9
(2008) 75–81.
[40] A. Romero, A. Santos, D. Escrig, E. Simon, Applied Catalysis A: General 392 (2011)
19–27.
[41] K.H. Prasad Reddy, R. Rahul, S. Sree Vardhan Reddy, B. David Raju, K.S. Rama Rao,
Catalysis Communications 10 (2009) 879–883.
[42] R. Shi, F. Wang, X. Mu, Y. Li, X. Huang, W. Shen, Catalysis Communications 11 (2009)
306–309.
[43] T. Mitsudome, Y. Mikami, K. Ebata, T. Mizugaki, K. Jitsukawa, K. Kaneda, Chemical
Communications (2008) 4804–4806.
[44] M. Dixit, M. Mishra, P.A. Joshi, D.O. Shah, Journal of Industrial and Engineering
Chemistry 19 (2013) 458–468.
References
[1] G. Guillena, D.J. Ramon, M. Yus, Angewandte Chemie International Edition 46
(2007) 2358–2364.
[2] T.D. Nixon, M.K. Whittlesey, J.M.J. Williams, Dalton Transactions (2009) 753–762.
[3] M.H.S.A. Hamid, P.A. Slatford, J.M.J. Williams, Advanced Synthesis and Catalysis
349 (2007) 1555–1575.
[4] G. Guillena, D.J. Ramon, M. Yus, Chemical Reviews 110 (2010) 1611–1641.
[5] A.J.A. Watson, J.M.J. Williams, Science 329 (2010) 635–636.
[6] F. Alonso, F. Foubelo, J.C. González-Gómez, R. Martínez, D.J. Ramón, P. Riente, M. Yus,
Molecular Diversity 14 (2010) 411–424.
[7] G.E. Dobereiner, R.H. Crabtree, Chemical Reviews 110 (2010) 681–703.
[8] S. Bahn, S. Imm, L. Neubert, M. Zhang, H. Neumann, M. Beller, ChemCatChem 3
(2011) 1853–1864.
[9] In: J. Otera (Ed.), Modern Carbonyl Chemistry, Wiley-VCH, Weinheim, 2000.
[10] M.B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Wiley, New York, 2001,
p. 499.
[11] R. Grigg, T.R.B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, Tetrahedron Letters 22
(1981) 4107–4110.
[45] F. Cavani, F. Trifiro, A. Vaccari, Catalysis Today 11 (1991) 173–301.
[12] C.S. Cho, B.T. Kim, T.-J. Kim, S.C. Shim, Journal of Organic Chemistry 66 (2001)
9020–9022.