Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen- transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse alpha-ketoesters or oxazetidines.

Automated summary

In this study, nitrosoarene was utilized as a mild oxygen source to oxidize an in situ generated carbene intermediate, enabling UV-light-mediated ketenes to react with nitrosoarenes and deliver oxazetidine derivatives. These simple processes highlight a transition-metal-free and catalyst-free protocol for obtaining structurally diverse alpha-ketoesters or oxazetidines.