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Synthesis of 1,3-diketones

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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.