Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of 1,3-diketones
Name Reactions
Baker-Venkataraman Rearrangement
Recent Literature
Ketones undergo soft enolate formation and acylation on treatment with MgBr2ˇOEt2,
i-Pr2NEt, and various acylating agents to give 1,3-diketones.
A particularly simple and efficient acylation with N-acylbenzotriazoles
and O-Pfp esters can be conducted in untreated, reagent-grade CH2Cl2
open to the air.
D. Lim, F. Fang, G. Zhou, D. M. Coltart, Org. Lett., 2007,
9, 4139-4142.
Mild and Efficient Pentafluorophenylammonium Triflate (PFPAT)-Catalyzed
C-Acylations of Enol Silyl Ethers or Ketene Silyl (Thio)Acetals with Acid
Chlorides
A. Iida, J. Osada, R. Nagase, T. Misaki, Y. Tanabe, Org. Lett., 2007,
9, 1859-1862.
Substituted 1,3-diketones were synthesized from α,β-unsaturated ketones by
treatment with acid chlorides and Et2Zn in the presence of RhCl(PPh3)3.
The reaction offers a very simple and chemoselective acylation at the α-position
of α,β-unsaturated ketones.
K. Sato, S. Yamazoe, R. Yamamoto, S. Ohata, A. Tarui, M. Omote, I. Kumadaki,
A. Ando, Org. Lett., 2008,
10, 2405-2408.
A recyclable, convenient, and efficient catalytic system allows the C-acylation
of 1,3-dicarbonyl compounds and malononitrile with acid chlorides in moderate to
excellent yields under mild conditions.
Q. Shen, W. Huang, J. Wang, X. Zhou, Org. Lett., 2007,
9, 4491-4494.
A convenient two-step preparation of alkylidenepyrrolidines is reported.
M. C. Elliot, S. V. Wordingham,
Synthesis, 2006, 1162-1170.
Various 1,3,5-tricarbonyl derivatives were prepared by a mild reaction of
1,3-bis(silyl enol ethers) with acid chlorides. Reactions of both aromatic and
aliphatic acid chlorides and bis(acid chlorides) were conducted.
T. Rahn, V. T. H. Nguyen, T. H. T. Dang, Z. Ahmed, K. Methling, M. Lalk, C.
Fischer, A. Spannenberg, P. Langer, J. Org. Chem., 2007,
72, 1957-1961.
