The Renaissance of Organo Nitriles in Organic Synthesis

Abstract

In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is of immense importance. The presence of nucleophilic N-atom, π-coordinating ability of the triple bond, and electrophilic C-center imparts unique and interesting reactivities. Owing to the ability of the nitrile to transform into various other functional groups or intermediates, the chemistry is very rich and diverse. In particular, the involvement of nitrile in numerous organic reactions such as inter- or intramolecular alkyne insertion, [2+2+2] cycloaddition with alkynes, [3+2] cycloaddition with azides, [4+2] cycloaddition with dienes allow the synthesis of many important carbo- and heterocycles. Furthermore, the nitrile serves as a directing group in many C-H bond functionalization reactions to introduce diverse functionalities and participate as a radical acceptor in radical cascade strategies to obtain a large variety of functional molecules. This review mainly focuses on the reactivity and diverse synthetic application of the nitrile including C-H bond functionalization, alkyne insertion, cycloaddition, and thermal or photochemical cascade strategy. The objective of the current review aims at bringing out the striking collection of various nitrile-triggered organic transformations.

Keywords: C−H bond functionalization; alkyne insertion; annulations; carbocycles; cycloadditions; heterocycles; nucleophilic or radical cascades.