Photocatalytic Activity of Triphenylphosphine and Potassium Iodide System in the Decarboxylative Alkylation of 3‐Cyanochromones

Abstract

The photocatalytic decarboxylative alkylation of 3-cyanochromones using triphenylphosphine and potassium iodide as photoredox-mediators has been described. The lower price of potassium iodide and triphenylphosphine, compared to standard photocatalysts, make this method cost-effective and interesting. Visible light, cheap and readily available substrates, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed transformation. The developed approach allows for obtaining a number of biologically relevant products with very good yields and benefits from a broad scope.

Synthesis of cyclopent-1-enecarbonitriles via a tandem Giese/HWE reaction initiated by visible light

“…9 The radical additions to electron-deficient olefins is known in the literature as a Giese reaction. 10–12 Recent significant advancements in this field arise from the development of photoinitiated methods allowing for the generation of radicals under mild and non-toxic conditions. An interesting way for the formation of radical species involves the usage of N -(acyloxy)phthalimide.…”

“…Given the importance of cyclopent-1-enes chemistry for both academic and industrial purposes and in continuation of our interest in the development of photocatalytic decarboxylative strategies, 11 vinyl phosphonates and N -(acyloxy)phthalimides systems have been proposed as convenient staring materials for their preparation (Scheme 2).…”