Litcius/Paper detail

Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes

Aleksandra Nilova, Bryan E. Metze, David R. Stuart

2021Organic Letters40 citationsDOI

Abstract

Arenes are broadly found motifs in societally important molecules. Access to diverse arene chemical space is critically important, and the ability to do so from common reagents is highly desirable. Aryl(TMP)iodonium tosylates provide one such access point to arene chemical space via diverse aryl intermediates. Here we demonstrate that controlling reaction pathways selectively leads to arynes with a broad scope of arenes and arynophiles (24 examples, 70% average yield) and efficient access to biologically active compounds.

Topics & Concepts

AryneArylChemistryReagentChemical spaceCombinatorial chemistryMoleculeYield (engineering)Function (biology)Organic chemistryDrug discoveryMaterials scienceMetallurgyBiologyEvolutionary biologyAlkylBiochemistryCyclization and Aryne ChemistryChemical synthesis and alkaloidsCatalytic Alkyne Reactions