Gao, HongyinZhou, ZheKwon, Doo-HyunCoombs, JamesJones, StevenBehnke, Nicole ErinEss, Daniel H.Kürti, László2017-01-272017-01-272016Gao, Hongyin, Zhou, Zhe, Kwon, Doo-Hyun, et al.. "Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds." <i>Nature Chemistry,</i> (2016) Springer Nature: http://dx.doi.org/10.1038/nchem.2672.https://hdl.handle.net/1911/93784Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C−C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (−NH2) and hydroxyl (−OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N−H and N−alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.engThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by Springer Nature.Journal articlehttp://dx.doi.org/10.1038/nchem.2672