Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of 1,3-diketones
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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.
Treatment of an γ-acyloxy-α,β-unsaturated ketone with bis(iodozincio)methane
leads to a novel tandem reaction consisting of three steps: 1,4-addition of the
dizinc reagent to the enone, intramolecular nucleophilic attack by the enolate
on the ester group, and Grob-type fragmentation of the adduct to give
1,3-diketones efficiently.
M. Sada, S. Matsubara, J. Am. Chem. Soc., 2010,
132, 432-433.
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 tandem addition of two molecules of zinc alkanoate to a carbonyl compound
gives a series of δ-hydroxy-β-ketoesters. The key to accelerate such a double
Reformatsky reaction is considered to be a complex-induced proximity effect of
the in situ generated zinc alkoxide coordinated with a bidentate amine. A
feature of the reaction system is its high tolerance of functional groups due to
the moderate nucleophilicity of organozinc reagents.
M. Mineno, Y. Sawai, H. Kanno, N. Sawada, H. Mizufune J. Org. Chem., 2013,
78, 5843-5850.
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.
Related
A short, mild, and highly chemoselective addition of organolithium reagents to
BF2 complexes of 3-oxopropanoates allows a straightforward
preparation 1,3-diketones.
B. Štefane, Org. Lett., 2010,
12, 2900-2903.
An oxidative coupling method for alkyne difunctionalization under
metal-catalyst-free conditions affords various β-ketodithianes in very good
yields with high regioselectivities. The reaction provides valuable dithianes
with controlled formation of a new C-C bond and a C-O bond via a radical
coupling pathway.
J. Lai, L. Tian, X. Huo, Y. Zhang, X. Xie, S. Tang, J. Org. Chem.,
2015,
80, 5894-5899.
