Promoted by gallium triiodide, an α-bromoketone, bromomethyl phenyl ketone, is treated with acyl chlorides to synthesize 1,3-diketones in good yields under mild and neutral conditions.
References
1.
BahrG., and BurhaP., Methoden zur Herstellung und Umwandlung Gallium-Organischer Verbindungen, in Houben-Weyl Methoden der Organischen Chemie, ed. MullerE., Georg Thieme Verlag, Stuttgart, 1970, vol. 13/14, pp. 319–341.
2.
ZweifelG., Organic Compounds of Group 3 Metals, in Comprehensive Organic Chemistry, ed. BartonD. H. R., and OllisW. D., Pergamon Press, Oxford, 1979, Vol. 3, part 15. 3, pp. 1013–1041.
3.
(a) HanY., and HuangY. Z., Tetrahedron Lett., 1998, 39, 7751; (b) Y. Han and Y. Z. Huang, Tetrahedron Lett., 1995, 36, 7277.
4.
KobayashiS., KoideK., and OhnoM., Tetrahedron Lett., 1990, 31, 2435 and references cited therein.
5.
HayashiA., YamaguchiM., and HiramaM., Synlett, 1995, 195 and references cited therein.
6.
ZhangX. L., HanY., TaoW. T., and HuangY. Z., J. Chem. Soc., Perkin Trans. 1, 1995, 189.
7.
HanY., and HuangY. Z., Tetrahedron Lett., 1994, 35, 9433.
8.
BaoW., and ZhangY., Synth. Commun., 1997, 27, 615.
9.
YingT., BaoW., ZhangY., and XuW., Tetrahedron Lett., 1996, 37, 3885.
10.
LinnB. O., and HauserC. R., J. Am. Chem. Soc., 1956, 78, 6066.
11.
BreslowD. S., and HauserC. I., J. Am. Chem. Soc., 1940, 62, 2385.
12.
MuirW. M., RitchieP. D., and LymanD. J., J. Org. Chem., 1966, 31, 3790.
13.
WuH., ChenR., and ZhangY., Synth. Commun., in press.
14.
YingT., BaoW., and ZhangY., Synth. Commun., 1996, 26, 2905.
15.
KatayamaS., FukudaK., WatanableT., and YamauchiM., Synthesis, 1988, 178.
