Chemodivergent phosphonylation of diazocarboxylates: light-on vs. light-off reactions

Abstract

By tapping into the divergent reactivity of diazocarboxylates under thermal and photocatalytic conditions, we could develop chemodivergent phosphonylation protocols for α-diazocarboxylates with trialkyl phosphites. While the thermal reaction led to N–P bond formation affording phosphonylated hydrazones, the visible light-mediated reaction furnished phosphonylated aryl carboxylates through C–P bond formation. Both reactions are notable for their operational simplicity and mild conditions affording products in good yields without the requirement of a metal, base or photocatalyst.