Organocatalytic Regioselective Synthesis of Sulfur-Containing N-Alkyl Carbamates from Alkyne-Derived Cyclic Carbonates
作者：Bin Liu and Xinghong Zhang
關鍵字：sulfur-containing N-alkyl carbamate,Alkyne-Derived Cyclic Carbonates
論文來源：期刊
具體來源：Gen. Chem. 2018, 4, 180007.
發表時間：2018年
A highly regioselective synthesis of sulfur-containing N-alkyl carbamate from propargyl alcohol, carbon dioxide (CO2) and amine via metal-free catalysis is described. The regioselective ring-opening addition of tri-substituted cyclic carbonate with amine was investigated in detail. A key feature of this system is the ability to afford tertiary β-hydroxyl N-alkyl carbamate with 100% selectivity by using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as the catalyst in a wide range of reaction temperatures. The steric hindrance of amine and the use of ethanol favored the regioselective ring-opening addition reaction. A proposed mechanism for the ring-opening
addition elaborated the underlying reason for the regioselective synthesis of sulfur-containing N-alkyl carbamate. This study provides a new alternative synthetic route to sulfur-containing N-alkyl carbamates from alkyne and CO2 and may offer an attractive scaffold for further synthesis.