Practical and regioselective amination of arenes using alkyl amines

Research output: Contribution to journalArticle

  • Authors:
  • Alessandro Ruffoni
  • Fabio Juliá
  • Thomas D. Svejstrup
  • Alastair J. Mcmillan
  • James J. Douglas
  • And 1 others
  • External authors:
  • Daniele Leonori

Abstract

The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.

Bibliographical metadata

Original languageEnglish
Pages (from-to)426-433
JournalNature Chemistry
Volume11
Issue number5
Early online date22 Apr 2019
DOIs
Publication statusPublished - May 2019