Palladium-catalyzed difluoroalkylation of aryl boronic acids: a new method for the synthesis of aryldifluoromethylated phosphonates and carboxylic acid derivatives.
The palladium-catalyzed difluoroalkylation of aryl boronic acids with bromodifluoromethylphosphonate, bromodifluoroacetate, and further derivatives has been developed. This method provides a facile and useful access to a series of functionalized difluoromethylated arenes (ArCF2 PO(OEt)2 , ArCF2 CO2 Et, and ArCF2 CONR(1) R(2) ) that have important applications in drug discovery and development. Preliminary mechanistic studies reveal that a single electron transfer (SET) pathway may be involved in the catalytic cycle.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China).
Zhang
Z
Feng
Qiao-Qiao
QQ
Min
Yu-Lan
YL
Xiao
Bo
B
Zhang
Xingang
X
Zhang
D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004579:Electron Transport; D004583:Electrons; D005461:Fluorine / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D001897:Boronic Acids; D002264:Carboxylic Acids; D063065:Organophosphonates; D005461:Fluorine; D010165:Palladium
aryl boronic acids; cross-coupling; difluoroalkylation; fluorine; palladium