Zhao Ligang, Lu Xiyan
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Org Lett. 2002 Oct 31;4(22):3903-6. doi: 10.1021/ol026741h.
[formula: see text] A divalent palladium-catalyzed coupling reaction of electron-deficient alkynes and acrolein or MVK (methyl vinyl ketone) was developed. The reaction provides an efficient method to synthesize gamma,delta-unsaturated carbonyls. A mechanism involving acetoxypalladation of alkyne, followed by insertion of alkene and protonolysis of the C-Pd bond, is proposed. The protonolysis of the carbon-palladium bond with the assistance of bidentate nitrogen containing ligands is the key step in this tandem reaction.
