Journal of the American Chemical Society 2013-09-25

Silver-catalyzed radical phosphonofluorination of unactivated alkenes.

Chengwei Zhang, Zhaodong Li, Lin Zhu, Limei Yu, Zhentao Wang, Chaozhong Li

Index: J. Am. Chem. Soc. 135(38) , 14082-5, (2013)

Full Text: HTML

Abstract

We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 °C led to the efficient synthesis of β-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.