American Chemical Society
jo3025237_si_001.pdf (2.38 MB)

Regioselective C–H Bond Cleavage/Alkyne Insertion under Ruthenium Catalysis

Download (2.38 MB)
journal contribution
posted on 2013-01-18, 00:00 authored by Yuto 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.