RSC Advances
Paper
HG/T2354-92. Melting points were measured with SGW X-4
melting point apparatus. 1H NMR (300, 400 or 600 MHz) spectra
were recorded in CDCl3. 1H NMR chemical shis are reported in
ppm (d) relative to tetramethylsilane (TMS) with the solvent
68, 4609; (k) K. M. Lakshmi, T. Parsharamulu and
S. V. Manorama, J. Mol. Catal. A: Chem., 2012, 365, 115; (l)
´
´
¨ }
´
S. Balogh, G. Farkas, J. Madarasz, A. Szollosy, J. Kovacs,
¨
F. Darvas, L. Urge and J. Bakos, Green Chem., 2012, 14,
resonance employed as the internal standard (CDCl3,
d
1146; (m) B. Ding, Z. Zhang, Y. Liu, M. Sugiya, T. Imamoto
and W. Zhang, Org. Lett., 2013, 15, 3690; (n) P. Bobal and
J. Bobalova, Molecules, 2013, 18, 2212.
3 For recent reviews about Hantzsch esters, see: (a) S. L. You,
Chem. – Asian J., 2007, 2, 820; (b) Z. Chao and S. L. You,
Chem. Soc. Rev., 2012, 41, 2498; (c) S. G. Ouellet,
A. M. Walji and D. W. C. MacMillan, Acc. Chem. Res., 2007,
40, 1327; (d) Z. Y. Wang and Z. J. Jiang, Asian J. Chem.,
2010, 22, 4141; (e) J. G. de Vries and N. Mrsic, Catal. Sci.
Technol., 2011, 1, 727.
4 (a) M. Fujji, K. Nakamura, S. Yasui, S. Oka and A. Ohno, Bull.
Chem. Soc. Jpn., 1987, 60, 2423; (b) M. Fujii, Bull. Chem. Soc.
Jpn., 1988, 61, 4029.
5 (a) Z. Zhang and P. R. Schreiner, Synthesis, 2007, 2559; (b)
J. F. Schneider, M. B. Lauber, V. Muhr, D. Kratzer and
J. Paradies, Org. Biomol. Chem., 2011, 9, 4323.
7.26 ppm). Data are reported as follows: chemical shi, multi-
plicity (s ¼ singlet, d ¼ doublet, q ¼ quartet, m ¼ multiplet),
coupling constants (Hz) and integration.13C NMR chemical
shis are reported in ppm from tetramethylsilane (TMS) with
the solvent resonance as the internal standard (CDCl3,
77.0 ppm).
General experimental procedures for the reduction of the
carbon–carbon double bond in conjugated alkenes reactions: a
solution of alkenes (0.2 mmol) and Hantzsch esters (0.24 mmol)
in water (2.0 mL) was stirred at 100 ꢀC for 24 h. Aer the reaction
mixtures were cooled to room temperature, the crude solution
was extracted with ethyl acetate (3 ꢂ 5 mL). The combined
organic layers were washed with brine and dried over anhydrous
Na2SO4. Aer removal of solvents under reduced pressure, the
residue was puried through column chromatograph on silica
gel to give the pure products.
6 Q. Liu, J. Li, X. X. Shen, R. G. Xing, J. Yang, Z. Liu and
B. Zhou, Tetrahedron Lett., 2009, 50, 1026.
7 J. Che and Y. Lam, Synlett, 2010, 16, 2415.
Acknowledgements
8 (a) J. W. Yang, M. T. H. Fonseca and B. List, Angew. Chem.,
Int. Ed., 2004, 43, 6660; (b) S. G. Ouellet, J. B. Tuttle and
D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 32; (c)
S. Mayer and B. List, Angew. Chem., Int. Ed., 2006, 45, 4193;
(d) N. J. A. Martin and B. List, J. Am. Chem. Soc., 2006, 128,
13368; (e) J. B. Tuttle, S. G. Ouellet and
D. W. C. MacMillan, J. Am. Chem. Soc., 2006, 128, 12662; (f)
T. J. Hoffman, J. Dash, J. H. Rigby, S. Arseniyadis and
J. Cossy, Org. Lett., 2009, 11, 2756.
9 (a) K. Akagawa, H. Akabane, S. Sakamoto and K. Kudo, Org.
Lett., 2008, 10, 2035; (b) K. Akagawa, H. Akabane,
S. Sakamoto and K. Kudo, Tetrahedron: Asymmetry, 2009,
20, 461; (c) N. J. A. Martin, L. Ozores and B. List, J. Am.
Chem. Soc., 2007, 129, 8976; (d) N. J. A. Martin, X. Cheng
and B. List, J. Am. Chem. Soc., 2008, 130, 13862.
We are grateful for the nancial supports from the National
Natural Science Foundation of China (21102115 and 81302647),
the spring plan of Ministry of Education (13233637), the
Sichuan Education Department (13ZA0206), the Science and
Technology Department of Chengdu (12DXYB001JH), the Key
Laboratory of Xihua University (Z1013314).
References
1 For reviews on reduction of C]C double bond, see: (a)
M. Hudlickey, Reductions in Organic Chemistry, American
Chemical Society, Washington, DC, 2nd edn, 1996; (b)
P. N. Rylander, Hydrogenation Methods, Academic, New
York, 1985; (c) J. Q. Li, X. Quan and P. G. Andersson, Chem.
–
Eur. J., 2012, 18, 10609; (d) T. L. Church and 10 Q. P. B. Nguyen, J. N. Kim and T. H. Kim, Tetrahedron, 2012,
P. G. Andersson, Coord. Chem. Rev., 2008, 252, 513; (e) 68, 6513.
T. Bolano, R. Castarlenas, M. A. Esteruelas and E. Onate, 11 For a nornicotine-catalyzed transfer hydrogenation of a,
J. Am. Chem. Soc., 2007, 129, 8850.
b-unsaturated aldehydes using 1,4-dihydropyridine-3,5-
dicarboxylic acid in aqueous solution, see: A. P. Brogan,
T. J. Dickerson and K. D. Janda, Chem. Commun., 2007,
4952.
2 For examples on reduction of C]C double bond, see: (a)
M. D. Bhor, M. J. Bhanushali, N. S. Nandurkar and
B. M. Bhanage, Catal. Commun., 2007, 8, 2064; (b) D. Xue,
Y. C. Chen, X. Cui, Q. W. Wang, J. Zhu and J. G. Deng, 12 J. Li, Z. Wang, Z. Jiang, S. Jiang and L. Xiong, Asian J. Chem.,
J. Org. Chem., 2005, 70, 3584; (c) M. Amiel-Levy and S. Hoz, 2011, 23, 4101.
J. Am. Chem. Soc., 2009, 131, 8280; (d) B. C. Ranu and 13 Some representative reviews on reaction in water: (a)
S. Samanta, Tetrahedron Lett., 2002, 43, 7405; (e)
Z. G. Zhang and P. R. Schreiner, Synthesis, 2007, 16, 2559;
(f) D. B. Ramachary, M. Kishor and Y. V. Reddy, Eur. J. Org.
Chem., 2008, 975; (g) D. B. Ramachary and M. S. Prasad,
Tetrahedron Lett., 2010, 51, 5246; (h) P. Chauhan, K. Kaur,
N. Bala, V. Kumar and S. S. Chimni, Indian J. Chem., 2011,
50B, 304; (i) Q. P. B. Nguyen, J. N. Kim and T. H. Kim,
Tetrahedron, 2012, 68, 6513; (j) J. Xiang, E. X. Sun,
T. Adschiri, Y. W. Lee, M. Goto and S. Takami, Green
Chem., 2011, 13, 1380; (b) Y. W. Wei, D. Xue, Q. Lei,
C. Wang and J. L. Xiao, Green Chem., 2013, 15, 629; (c)
M. Bakherad, Appl. Organomet. Chem., 2013, 27, 125; (d)
L. A. de Cienfuegos, R. Robles, D. Miguel and J. Justicia,
ChemSusChem, 2011, 4, 1035; (e) K. Kumaravel and
G. Vasuki, Curr. Org. Chem., 2009, 13, 1820; (f) M. Raj and
V. K. Singh, Chem. Commun., 2009, 44, 6687.
C. X. Lian, Q. W. Wang and J. G. Deng, Tetrahedron, 2012, 14 C. Hansch, A. Leo and R. W. Ta, Chem. Rev., 1991, 91, 165.
8674 | RSC Adv., 2014, 4, 8671–8674
This journal is © The Royal Society of Chemistry 2014