Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Hongyin Gao, Zhe Zhou, Doo Hyun Kwon, James Coombs, Steven Jones, Nicole Erin Behnke, Daniel H. Ess, László Kürti

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)681-688
Number of pages8
JournalNature Chemistry
Volume9
Issue number7
DOIs
StatePublished - Jul 1 2017

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Fingerprint Dive into the research topics of 'Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds'. Together they form a unique fingerprint.

  • Cite this

    Gao, H., Zhou, Z., Kwon, D. H., Coombs, J., Jones, S., Behnke, N. E., Ess, D. H., & Kürti, L. (2017). Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds. Nature Chemistry, 9(7), 681-688. https://doi.org/10.1038/nchem.2672