1
942
F. Alonso et al. / Tetrahedron Letters 49 (2008) 1939–1942
7. Le Page, M. D.; James, B. R. Chem. Commun. 2000, 1647–1648.
References and notes
8
9
. Phukan, P.; Sudalai, A. Synth. Commun. 2000, 30, 2401–2405.
. Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-
Ronchi, A. J. Org. Chem. 1985, 50, 3082–3086.
1
. For reviews, see: (a) Johnstone, R. A. W.; Wilby, A. H. Chem. Rev.
1
985, 85, 129–170; (b) Kellogg, R. M. In Comprehensive Organic
1
1
1
0. Upadhya, T. T.; Katdare, S. P.; Sabde, D. P.; Ramaswamy, V.;
Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991;
Vol. 8, Chapter 1.3; (c) B a¨ ckvall, J. E. J. Organomet. Chem. 2002, 652,
Sudalai, A. Chem. Commun. 1997, 1119–1120.
1. Mohapatra, S. K.; Sonavane, S. U.; Jayaram, R. V.; Selvam, P. Org.
Lett. 2002, 24, 4297–4300.
1
05–111; (d) Hydrogen Transfer Reactions; Hynes, J. T., Klinman, J.
P., Limbach, H. H., Schowen, R. L., Eds.; Wiley-VCH: Weinheim,
007.
2. (a) Mebane, R. C.; Mansfield, A. J. Synth. Commun. 2005, 35, 3083–
2
3
086; (b) Mebane, R. C.; Holte, K. L.; Gross, B. H. Synth. Commun.
2
3
. For reviews, see: (a) Ohkuma, T.; Noyori, R. In Comprehensive
Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H.,
Eds.; Springer: Berlin, 1999; Vol. I, pp 227–246; (b) Gladiali, S.;
Mestroni, G. In Transition Metals for Organic Synthesis; Beller, M.,
Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, Chapter 1.3.
. See for instance: (a) Nindakova, L. O.; Shainyan, B. A.; Belogonova,
L. N. Russ. J. Org. Chem. 2003, 39, 1484–1488; (b) Enthaler, S.;
Jackstell, R.; Hagemann, B.; Junge, K.; Erre, G.; Beller, M. J.
Organomet. Chem. 2006, 691, 4652–4659; (c) Wu, X.; Liu, J.; Li, X.;
Zanotti-Gerosa, A.; Hancock, F.; Vinci, D.; Ruan, J.; Xiao, J. Angew.
Chem., Int. Ed. 2006, 45, 6718–6722.
2
007, 37, 2787–2791.
1
3. (a) Alonso, F.; Calvino, J. J.; Osante, I.; Yus, M. Chem. Lett. 2005,
4, 1262–1263; (b) Alonso, F.; Calvino, J. J.; Osante, I.; Yus, M. J.
3
Exp. Nanosci. 2006, 1, 419–433.
1
1
4. Alonso, F.; Riente, P.; Yus, M. Tetrahedron 2008, 64, 1847–1852.
5. In a typical procedure: Nickel chloride (130 mg, 1 mmol) was added
over a suspension of lithium (14 mg, 2 mmol) and DTBB (13 mg,
0
.05 mmol) in dry THF (2 mL) at room temperature under argon.
The reaction mixture, which was initially dark blue, changed to black
indicating that nickel(0) nanoparticles were formed. After 10 min,
i-PrOH (4 mL) and the corresponding carbonyl compound (5 mmol)
were successively added. The reaction mixture was warmed up to
4
. For reviews, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997,
3
0, 97–102; (b) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol.
Chem. 2006, 4, 393–406; (c) Gladiali, S.; Alberico, E. Chem. Soc. Rev.
006, 35, 226–236.
. (a) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001,
6, 7931–7944; (b) Clapham, S. E.; Hadzovic, A.; Morris, R. H.
7
6 °C and monitored by GLC–MS until total or steady conversion of
the starting material. The resulting suspension was diluted with
diethyl ether (20 mL), filtered through a pad containing Celite, and
2
5
the filtrate was dried over MgSO
of the solvent (15 Torr) was purified by column chromatography
silica gel, hexane/EtOAc) to give the corresponding pure alcohol.
4
. The residue obtained after removal
6
Coord. Chem. Rev. 2004, 248, 2201–2237; (c) Samec, J. S. M.;
B a¨ ckwall, J.-E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006,
3
(
1
6. The deactivation of some common heterogeneous hydrogenation
catalysts (e.g., Pd/C and Raney Ni) after aging them in alcoholic
solvents has been recently reported: Singh, U. K.; Krska, S. W.; Sun,
Y. Org. Process Res. Dev. 2006, 10, 1153–1156.
5, 237–248.
6. For a recent review on heterogeneous metal catalysts, see: Kaneda,
K.; Ebitani, K.; Mizugaki, T.; Mori, K. Bull. Chem. Soc. Jpn. 2006,
79, 981–1016.