Decatungstate-photocatalyzed tandem acylation/cyclization/self-hydrogenation of isocyanides with aldehydes to hydroxyalkylated N-heteroarenes via multiple hydrogen atom transfer

Abstract

Both preventing the production of waste and achieving high atom economy are fundamental principles of green chemistry. Herein, the first example of a 100% atom economical construction of hydroxyalkylated N-heteroarenes, done through recyclable decatungstate-photocatalyzed tandem cyclization/self-hydrogenation of isocyanides with equimolar amounts of aldehydes without exogenous hydrogen reagent and under byproduct-free conditions, was developed. Mechanistic studies revealed that three sequential hydrogen atom transfer processes might be involved in this reaction and all the leaving hydrogens as hydrogen sources were incorporated into the target hydroxyalkylated products.