A variety of chalcones is rapidly reduced to the corresponding tetrahydrochalcones in high yields with nickel boride, generated in situ, in dry methanol at ambient temperature. The halo, methoxy and methyl groups remain unaffected under these conditions.
AdamsR., KernJ.W., and ShrinerR.L., Org. Synth. Coll., 1941, I, 101.
2.
RondestvedtC.S., J. Am. Chem. Soc., 1951, 73, 4509.
3.
BushbyR.J., and FerberG.J., J. Chem. Soc. Perkin Trans. II, 1976, 1683.
4.
(a) PetrierC., and LucheJ-L., Tetrahedron Lett., 1987, 28, 2347; (b) F. Alonso and M. Yus, Tetrahedron., 1998, 54, 1921; (c) G. Laval and B.T. Golding, Synlett., 2003, 279; (d) S. Saito and H. Yamamoto, J. Org. Chem., 1996, 61, 2928; (e) C.M. Belisle, Y.M. Young and B. Singaram, Tetrahedron Lett., 1994, 35, 5595; (f) T. Hase, Acta Chem. Scand., 1969, 23, 2403; (g) X. Cai and W. Hu, Shenyang Huagong Xueyuan Xuebero, 2004, 18, 303 (Chem. Abs., 2005, xx, 287615).
5.
(a) AraminiA., BrinchiL., GerminiR., and SavelliG., Eur. J. Org. Chem., 2000, 1793; (b) J.G. Handique, A. Purkayashtha and J.B. Baruah, J. Organometal. Chem., 2001, 620, 90; (c) B.C. Ranu and S. Samanta, Tetrahedron lett., 2003, 44, 7901.
6.
(a) GanemB., and OsbyJ.O., Chem. Rev., 1986, 86, 763; (b) J.M. Khurana and A. Gogia, Org. Prep. Proced. Int., 1997, 29, 1.
7.
(a) KhuranaJ.M., RayA., and SinghS., Tetrahedron Lett., 1998, 39, 3829; (b) J.M. Khurana and S. Chauhan, Synth. Commun., 2001, 31, 3485; (c) J.M. Khurana and G. Kukreja, Synth. Commun., 2002, 32, 1265; (d) J.M. Khurana and S. Chauhan, J. Chem. Res. (s), 2002, 201; J. Chem. Res. (M), 2002, 519; (e) J.M. Khurana, G. Kukreja and G. Bansal, J. Chem. Soc., Perkin Trans. 1, 2002, 2520; (f) J.M. Khurana and G. Kukreja, J. Heterocyclic Chem., 2003, 40, 677.
8.
(a) JohnsonM.R., and RickbornB., J. Org. Chem., 1970, 35(4), 1041; (b) R.S. Verma and L.W. Kabelka, Synth. Commun., 1985, 15, 985.
9.
(a) KarabuhetH.R., KecanM., and OezyildirimH., Turk. J. Chem., 2003, 27, 713; (b) C.S. Chao, B.T. Kim, H.S. Kim and S.C. Shim, Organometallics, 2003, 22, 3608.
