A mild and efficient addition of ethynylbenzene with ketones using KOH in ionic liquid 1-butyl-3-methylimidazolium hexaflurophosphate [(bmim) PF6] gives propargylic alcohols in high yields.
(a) FriedJ., LinC., MehroM., KaoW., and DahrenP., Ann. N. Y. Acad. Sã., 1971, 180, 38; (b) W.S. Johnson, R.S. Brinkmeyer, U.M. Kapoor and T.L. Yarnell, J. Am. Chem. Soc., 1977, 99, 8341; (c) K.K. Chan, N.C. Cohen, J.P. Denoble, A.C. Speãan and G. Saucy, J. Org. Chem., 1976, 41, 3497.
2.
(a) FridrichK., In The Chemistry of Triple-bonded Functional Groups, Supplement C; PataiS., and RappoportZ., (eds.); John Wiley & Sons, New York, 1983; Chap. 28; (b) L. Brandsma and H.D. Verkruijsse, Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1981, p.3.
3.
YagamuchiM., HayashiA., and HiramaM., Chem. Lett., 1992, 2479.
4.
HanY., and HuangY.Z., Tetrahedron Lett., 1995, 36, 7277.
5.
YagamuchiM., HayashiA., and MinamiT., J. Org. Chem., 1991, 56, 4091.
6.
(a) AnandN.K., and CarreiraE.M., J. Am. Chem. Soc., 2001, 123, 9687; (b) J. Biao and Y.G. Si, Tetrahedron Lett., 2002, 43, 8323.
7.
TeruhikoI., TomohiroM., KumikoH., ToshiakiA., TakayukiK., and SeikiS., J. Org. Chem., 2003, 68, 3702.
8.
SharifiA., MirzaeiM., and JamalM., Synthetic Commun., 2005, 35, 1039.
9.
TazilsD., and KnochelP., Angew.Chem., Int. Ed., 1999, 38, 1463.
10.
BablerJ.H., LiptakV.P., and PhanN.J. Org. Chem., 1996, 61, 416.
11.
WasserscheidP., and KeimW., Angew. Chem., Int. Ed., 2000, 39, 3772.
12.
SteinesS., Drieben-HolscherB., and WasserscheidP., J. Prakt. Chem., 2000, 342, 348.
13.
ChauvinY., OliverH., and MubamannL., FR 95/14, 147, 1995; [Chem. Abstr. 1997, 127, P 341298k].
14.
SongC.E., and RohE.J., Chem. Commun., 2000, 837.
15.
MiyamotoH., YasakaS., and TanakaK., Bull Chem. Soc., 2001, 74, 185.
16.
IshikawaT., MizutaT., HagiwaraK., AikawaT., KudoT., and SaitoS., J. Org. Chem., 2003, 68, 3702.
