Categories: C-C Bond Formation > Oxygen-containing molecules, Alkynes >
Synthesis of alkynyl ketones, carboxylic acids and derivatives
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Recent Literature
A polystyrene-supported zinc bromide-ethylenediamine complex is a useful,
recyclable heterogeneous catalyst for the rapid and efficient synthesis of
α,β-acetylenic ketones in very good yields by cross coupling of acid chlorides
with terminal alkynes. The catalyst is easily prepared, stable, reusable, and
efficient under the reaction conditions.
A. Keivanloo, M. Bakherad, B. Bahramian, M. Rahmani, S. A. N. Taheri, Synthesis, 2011,
325-329.
A selective coupling of alkynylsilanes and allyltrimethylsilane is catalyzed
by 5 mol% of indium tribromide under mild conditions to afford the
corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in
excellent yields.
J. S. Yadav, B. V. S. Reddy, M. Sridhar Reddy, G. Parimala, Synthesis,
2003, 2390-2394.
Carbonylative coupling of terminal alkynes with aryliodides in the presence of
PdCl2(PPh3)2
as catalyst in 2 eq. of 0.5 M aqueous ammonia, and CO (1 atm) gives the
corresponding α,β-alkynyl ketones in good yields.
M. S. M. Ahmed, A. Mori, Org. Lett., 2003,
5, 3057-3060.
A Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction at
room temperature was achieved by using water as a solvent under balloon
pressure of CO with Et3N as a base.
B. Liang, M. Huang, Z. You, Z. Xiong, K. Lu, R. Fathi, J. Chen, Z. Yang,
J. Org. Chem., 2005,
70, 6097-6100.
Alkynyldimethylaluminum reagents react efficiently with various aromatic and
aliphatic acid chlorides without any transition metal as a catalyst to give
ynones in good yields.
B. Wang, M. Bonin, L. Micouin, J. Org. Chem., 2005,
70, 6126-6128.
2-Oxo-3-butynoates and 2-oxo-3-butynoamides were synthesized by a general,
efficient and mild Cu(I)-catalyzed cross-coupling of terminal alkynes and
monooxalyl chloride derivatives. Readily available starting materials, mild
reaction conditions, wide functional group tolerance, and the obviation of
stoichiometric organometallic reagents combine to highlight this reaction.
M. Guo, D. Li, Z. Zhang, J. Org. Chem., 2003, 68,
10172-10174.
