Organophosphites: An Addition to the Arsenal of Organocatalysts

Organophosphites are nucleophilic in nature and can act as a good leaving group owing to the stability of the phosphite anion. This dual reactivity makes them good candidates for nucleophilic organocatalysis. However, phosphites were introduced only in 2004 as the umpolung catalyst for acylsilane substrates utilizing sequential Brook rearrangements. Very recently, phosphites have been reported to catalyze aza-rearrangements and radical reactions. In this review, we discuss the reactivity parameters to understand its lack of use, as well as the potential for catalysis.

Automated summary

Organophosphites are nucleophilic and can act as good leaving groups, making them suitable for nucleophilic organocatalysis. However, they were only introduced as umpolung catalysts in 2004 for acylsilane substrates. Recently, they have also been reported to catalyze aza-rearrangements and radical reactions. In this review, their lack of use and potential for catalysis are discussed.