Categories: C-C Bond Formation > Oxygen-containing molecules, Alkynes >
Synthesis of propargyl ketones, carboxylic acids and derivatives
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Recent Literature
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.
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.
