Highly regio- and stereoselective hydrophosphinylation of acetylenes with diphenylphosphine oxide catalyzed by immobilization of rhodium in MCM-41

Highly regio- and stereoselective hydrophosphinylation of a wide range of acetylenes with diphenylphosphine oxide was achieved in toluene at 70 °C in the presence of 2 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex [MCM-41-2P-RhCl(PPh3)], yielding a variety of (E)-alkenylphosphine oxides in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity or selectivity.

Graphical abstractHighly regio- and stereoselective hydrophosphinylation of a wide range of acetylenes with diphenylphosphine oxide was achieved in toluene at 70 °C in the presence of 2 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex [MCM-41-2P-RhCl(PPh3)], yielding a variety of (E)-alkenylphosphine oxides in good to excellent yields.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► MCM-41-2P-RhCl(PPh3) complex was first investigated in hydrophosphinylation of alkynes. ► This heterogeneous phosphine rhodium complex exhibited high catalytic activity. ► This rhodium catalyst can be reused at least 10 times without any decrease in activity. ► Our catalytic system provides a practical route to the synthesis of (E)-alkenylphosphine oxides.