Journal of Organic Chemistry p. 2549 - 2553 (1982)
Update date:2022-08-24
Topics:
Logue, Marshall W.
Teng, Kelly
Acyl chlorides couple with (1-alkynyl)tributylstannanes in the presence of catalytic amounts of palladium(II) or palladium(0) complexes to produce 1-alkynyl ketones in respectable yields.The couplings of isobutyryl, acetyl, benzoyl, and p-nitrobenzoyl chlorides with phenylethynyl-, (trimethylsilyl)ethynyl-, (carbomethoxy)ethynyl-, <3-<(tert-butyldimethylsilyl)oxy>-1-propynyl>-, and (3,3-diethoxy-1-propynyl)tributylstannanes were investigated in the presence of tetrakis(triphenylphosphine)palladium(O), benzylchlorobis(triphenylphosphine)palladium(II), dichlorobis(triphenylphosphine)palladium(II), or phenyliodobis(triphenylphosphine)palladium(II).The reactions are highly selective in that only the alkynyl groups are transferred from the stannane.
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