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Synthesis of β-Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N-H Heterocycles.

Daniel FrancisAdam NelsonStephen P Marsden
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
3-Amino-substituted saturated nitrogen heterocycles are an important subclass of β-diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox-mediated hydroamination of enecarbamates. The amine coupling partner can encompass diverse amine types under a single set of reaction conditions, including primary alkyl amines, ammonia, aryl and heteroaryl amines, and N-H heterocycles. The method enables the synthesis of a wide range of pharmaceutically relevant building blocks.
Keyphrases
  • visible light
  • room temperature
  • anaerobic digestion
  • ionic liquid
  • molecular docking
  • electron transfer
  • molecular dynamics simulations
  • amino acid