A catalytic reaction of alkynes via multiple-site functionalization.
The first multiple-site activation of alkynes with amine/halogen functionalities has been established. The reaction was performed by treating alkyne with N,N-dichlorobenzenesulfonamide at 80 degrees C in the presence of palladium acetate catalyst. A new mechanism was proposed which involves the novel formation of beta-halovinyl palladium and pi-allylpalladium species. Excellent regio- and stereoselectivities were achieved with the absolute structure determined by X-ray structural analysis.
Karur
Subramanian
S
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Kotti
S R S Saibabu
SR
Xu
Xin
X
Cannon
John F
JF
Headley
Allan
A
Li
Guigen
G
D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D010165:Palladium / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D010165:Palladium