Catalysis Letters, Vol.148, No.2, 642-652, 2018
Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids
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 H-1- and C-13-NMR, MS, melting point, IR and CHNS techniques. Graphical Abstract [GRAPHICS] .
Keywords:Primary carbamates;N-Arylation;Cross-coupling;Copper iodide;Alkyl arylcarbamates;Secondary carbamates