Vol.:(0123456789) 1 3 Catalysis Letters https://doi.org/10.1007/s10562-017-2277-0 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 1  · Iman DindarlooInaloo 1  · Milad Zangiabadi 1 Received: 30 September 2017 / Accepted: 8 December 2017 © Springer Science+Business Media, LLC, part of Springer Nature 2017 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 1 H- and 13 C-NMR, MS, melt- ing point, IR and CHNS techniques. Graphical Abstract Keywords Primary carbamates · N-Arylation · Cross-coupling · Copper iodide · Alkyl arylcarbamates · Secondary carbamates 1 Introduction N-Substituted carbamates are an attractive class of chemi- cal compounds due to their widespread applications [1–4]. The biological effects of these substances have been dis- closed greatly in many pharmaceutical compounds like anti-diabetic, anti-estrogenic, anticancer, anti-inflammatory, Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-017-2277-0) contains supplementary material, which is available to authorized users. * Ali Reza Sardarian sardarian@shirazu.ac.ir 1 Chemistry Department, College of Sciences, Shiraz University, Shiraz 71946 84795, Iran