3 years ago

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
Steven Jones, James Coombs, Doo-Hyun Kwon, Zhe Zhou, Nicole Erin Behnke, Daniel H. Ess, Hongyin Gao, László Kürti
Arylmetals 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.

Publisher URL: http://dx.doi.org/10.1038/nchem.2672

DOI: 10.1038/nchem.2672

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