Palladium-catalyzed allylic alkylation of simple ketones with allylic alcohols and its mechanistic study.
Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier.
School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (China) http://wanbin.sjtu.edu.cn.
Xiaohong
X
Huo
Guoqiang
G
Yang
Delong
D
Liu
Yangang
Y
Liu
Ilya D
ID
Gridnev
Wanbin
W
Zhang
D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013816:Thermodynamics
D000447:Aldehydes; D056831:Coordination Complexes; D007659:Ketones; D020005:Propanols; C006463:allyl alcohol; D010165:Palladium; D000432:Methanol
DFT calculation; allylic alcohol; allylic alkylation; organocatalysis; palladium