Radical Cation Salt‐initiated Aerobic C−H Phosphorylation of N‐Benzylanilines: Synthesis of α‐Aminophosphonates

Abstract

A radical cation salt-initiated phosphorylation of N-benzylanilines was realized through an aerobic oxidation of the sp C-H bond, providing a series of α-aminophosphonates in high yields. An investigation of the reaction scope revealed that this mild catalyst system is superior in good functional group tolerance and high reaction efficiency. The mechanistic study implied that the cleavage of the sp C-H bond was involved in the rate-determining step.

Recent Advances in C(sp3)—H Phosphorylation Based on Secondary Phosphine Oxides and Phosphite Esters

“…Soon after, this strategy was then applied to the phosphorylation of N-benzylanilines by the same group (Entry 2). [55] The group of Xiong [56] realized the phosphorylation of secondary N-alkyl anilines by using DDQ as an oxidant under metal-free conditions (Entry 3). A similar transformation for allylamines was then achieved by the group of Cheng (Entry 4).…”