Palladium-Catalyzed Methylation of Nitroarenes with Methanol

Lin Wang, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

Abstract

A procedure for the synthesis of N-methyl-arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1-[2,6-bis(isopropyl)phenyl]-2-[tert-butyl(2-pyridinyl)phosphino]-1H-Imidazole (L1). The generality of this protocol is demonstrated in the synthesis of more than 20 N-methyl-arylamines under comparably mild conditions. Combining this novel methodology with subsequent coupling processes using the same catalyst allows for efficient diversification of aromatic nitro compounds to a broad variety of amines including drug molecules.

Original languageEnglish
Pages (from-to)5417-5421
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume58
Issue number16
DOIs
StatePublished - 8 Apr 2019
Externally publishedYes

Keywords

  • N-methylation
  • functionalization
  • methanol
  • monophosphines
  • reaction mechanism

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