posted on 2013-01-18, 00:00authored byYuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, Masahiro Miura
The ruthenium-catalyzed coupling reactions of benzamides
with alkynes
in the presence of acetic acid as a promoter smoothly proceeded regio-
and stereoselectively through a directed C–H bond cleavage
to produce the corresponding ortho-alkenylated products.
Phenylpyrazoles and related substrates also underwent a similar coupling
to give dialkenylated products selectively. Several competitive experiments
were performed to obtain mechanistic insight into both the mono- and
dialkenylation reactions.