Thiol-promoted selective addition of ketones to aldehydes.
A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.
Department of Chemistry, Ben-Gurion University of the Negev , Beer-Sheva 84105, Israel.
Regev
R
Parnes
Sachin
S
Narute
Doron
D
Pappo