The Reactivity of Acceptor-Acceptor Diazo Pyrazolones with Allyl Thioethers under Visible Light: Access to Homoallyl Sulfides, Spiropyrazolones - Pesticide Analogues and Photoflow Synthesis

Abstract

The novel reactivity of a less selective and more reactive acceptor-acceptor kind of diazo pyrazolone (DIPOL) has been explored under visible light for the first time. We have successfully demonstrated the reaction of DIPOL and different allyl thioethers under blue light to construct a wide variety of products including a pesticidal analogue exclusively in excellent chemoselectivity in good to excellent yields. Moreover, possible side products emanating from ketene were not observed. This protocol works smoothly in an environmentally benign solvent under inert free conditions. The practicality of the protocol has been extended to a photoflow reaction, and also, the reaction works smoothly under the direct exposure of sunlight