Growing Impact of Intramolecular Click Chemistry in Organic Synthesis

Chem Rec. 2023 Nov;23(11):e202300167. doi: 10.1002/tcr.202300167. Epub 2023 Jul 31.

Abstract

Click Chemistry, a modular, rapid, and one of the most reliable tool for the regioselective 1,2,3-triazole forming [3+2] reaction of organic azide and terimal alkyne is widely explored in various emerging domains of research ranging from chemical biology to catalysis and medicinal chemistry to material science. This regioselective reaction from a diverse range of azido-alkyne scaffolds has been well performed in both intermolecular as well as intramolecular fashions. In comparison to the intermolecular metal (Cu/Ru/Ni) variant of 'Click Chemistry', the intramolecular click tool is little addressed. The intramolecular click chemistry is exemplified as a mordern tool of cyclization which involves metal-catalyzed (CuAAC/RuAAC) cyclization, organo-catalyzed cyclization, and thermal-induced topochemical reaction. Thus, we report herein the recent approaches on intramolecular azide-alkyne cycloaddition 'Click Chemistry' with their wide-spread emerging applications in the developement of a diverse range of molecules including fused-heterocycles, well-defined peptidomemics, and macrocyclic architectures of various notable features.

Keywords: Alkyne; Azides; Click Chemistry; CuAAC; Intramolecular Cyclization; Regioselectivity; RuAAC; Triazole; macrocyclization.

Publication types

  • Review