Self-propagating Pudovik reaction using phosphonic acid-based catalysts

The design of novel organocatalysts continues to be an active field of organic synthesis. Here, we present a series of substituted α-hydroxy- and α-amino phosphonic acids as novel organocatalysts in the hydrophosphination (Pudovik reaction) of aldehydes with dialkyl phosphites. Notably, the reaction is designed with a self-propagating feature, whereby the obtained α-hydroxy- and α-amino phosphonates can be hydrolyzed into phosphonic acids that serve as catalysts for subsequent iteration of the Pudovik reaction. The results presented herein may stimulate the development of novel organocatalysts based on the phosphonic acid functional group.