Stereoselective Synthesis of Monofluoroalkenylphosphine Oxides via Photoinduced Decarboxylative Coupling of α-Fluoroacrylic Acids with P(O)H Compounds
Xiaoyu Lu, Hong-Ye Pan, Rui Huang, Kang Yang, Xiang Zhang, Zizhen Wang, Qian-Qian Tao, Gui-Xian Yang, Xiaojuan Wang, Haipin Zhou
Abstract
Herein, a practical and efficient method for synthesizing monofluoroalkenyl phosphine oxides via photoinduced decarboxylative/dehydrogenative coupling of α-fluoroacrylic acids with phosphine oxides and phosphonates has been developed. Various α-fluoroacrylic acids and P(O)H compounds containing relevant functional groups, including tetrafluorobenzene and pentafluorobenzene, were converted into corresponding products with excellent E -stereoselectivity in satisfactory yields. This method can be extended to achieve the synthesis of monofluoroalkenyl silanes under similar conditions.
Topics & Concepts
ChemistryStereoselectivitySilanesPhosphineCoupling (piping)Combinatorial chemistryOrganic chemistryCatalysisSilaneEngineeringMechanical engineeringFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions