Truce–Smiles Rearrangements by Strain Release: Harnessing Primary Alkyl Radicals for Metal‐Free Arylation
David M. Whalley, Jayasree Seayad, Michael F. Greaney
Abstract
Abstract The ring‐opening of 3‐aminocyclobutanone oximes enables easy generation of primary alkyl radicals, capable of undergoing an unprecedented strain‐release, desulfonylative radical Truce–Smiles rearrangement, providing divergent access to valuable 1,3 diamines and unnatural β‐amino acids. Characterized by mild conditions and wide scope of migrating species, this protocol allows the modular assembly of sp 3 ‐aryls under transition metal‐free, room‐temperature conditions.
Topics & Concepts
RadicalAlkylPrimary (astronomy)ChemistryStrain (injury)MetalScope (computer science)Modular designRing (chemistry)StereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryBiologyComputer scienceAstronomyOperating systemAnatomyProgramming languagePhysicsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions