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Catalysis Letters

, Volume 148, Issue 2, pp 642–652 | Cite as

Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids

  • Ali Reza Sardarian
  • Iman DindarlooInaloo
  • Milad Zangiabadi
Article

Abstract

An efficient, selective and cost-effective procedure has been developed for mono N-arylation of primary alkyl and benzyl carbamates with aryl iodides and bromides by incorporating CuI as an inexpensive and commercially available catalyst. Despite previous reports on C–N coupling reactions, this process does not need expensive ligands and takes advantage of readily available and inexpensive ethylenediamine (EDA) as the ligand. Reaction times were relatively short and related N-arylated carbamates were obtained in excellent yields. Interestingly, replacing CuI with Cu(OAc)2 allowed us to use arylboronic acids as coupling partner for this reaction. All products are well characterized by 1H- and 13C-NMR, MS, melting point, IR and CHNS techniques.

Graphical Abstract

Keywords

Primary carbamates N-Arylation Cross-coupling Copper iodide Alkyl arylcarbamates Secondary carbamates 

Notes

Acknowledgements

Authors gratefully acknowledge the financial support of this work by the research council of Shiraz University.

Supplementary material

10562_2017_2277_MOESM1_ESM.doc (7.3 mb)
Supplementary material 1 (DOC 7485 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Ali Reza Sardarian
    • 1
  • Iman DindarlooInaloo
    • 1
  • Milad Zangiabadi
    • 1
  1. 1.Chemistry Department, College of SciencesShiraz UniversityShirazIran

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