J. Dheur, M. Sauthier, Y. Castanet
Nov 5, 2007
Citations
1
Influential Citations
26
Citations
Journal
Advanced Synthesis & Catalysis
Abstract
The carbonylative addition of arylboronic acids to terminal alkynes under mild conditions affords (E)-α,β-unsaturated ketones with good yields. The reaction was achieved with chloro(1,5-cyclooctadiene)rhodium(I) dimer or chlorodicarbonylrhodium(I) dimer as catalytic precursor without additional phosphine as their use inhibits the reaction. Experiments using deuterated 1-hexyne discarded the possibility of a rhodium-vinylidene intermediate, thus a catalytic cycle involving a 1,2-insertion of the terminal alkyne in a rhodium-acyl bond is proposed. This new reaction represents the first example of the hydroacylation of terminal alkynes involving rhodium-acyl reagents generated under CO pressure and promises a wide field of interest.