Visible light-assisted chemistry of vinyl azides and its applications in organic synthesis

Abstract

Vinyl azides have emerged as highly versatile precursors in organic synthesis due to their rich reactivity driven by the excellent leaving-group ability of molecular nitrogen. Over the years, significant advancement has been achieved in the manipulation of vinyl azides for the construction of C–C and C–X bonds. Typical methods involve the application of transition metals and strong oxidants for the conversion of vinyl azides into useful compounds employing harsh reaction conditions coupled with intense product purification. In this regard, visible light chemistry has become one of the most exciting fields in organic synthesis for being mild, sustainable, and often orthogonal to conventional approaches. Visible light-induced reactions involving vinyl azides generate either 2H-azirines or iminyl radicals as key intermediates, which may undergo further useful transformations to form the desired cyclic or acyclic products. Herein, we provide the most significant transformations of vinyl azides as versatile synthetic precursors or transient intermediates for compounds of synthetic and biological significance under visible light photocatalysis. We have classified this review into two parts: (i) formation of an iminyl radical intermediate and (ii) formation of 2H-azirine intermediate-based reactions.