Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation
Michael F. Greaney, David M. Whalley
Abstract
Abstract The Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This short review will discuss recent applications of the reaction (from 2017 to late 2021), including its relevance to areas such as heterocycle synthesis and the functionalization of alkenes and alkynes as well as glimpses at new directions for the field. 1 Introduction 2 Polar Smiles Rearrangements 3 Radical Smiles: Alkene and Alkyne Functionalization 4 Radical Smiles: Rearrangements via C–X Bond Cleavage 5 Radical Smiles: Miscellaneous Rearrangements 6 Conclusions
Topics & Concepts
Smiles rearrangementChemistryAlkeneCleavage (geology)AlkyneThe RenaissanceStereochemistryOrganic chemistryArt historyCatalysisEngineeringFracture (geology)ArtGeotechnical engineeringCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsPhenothiazines and Benzothiazines Synthesis and Activities