Organocatalytic Regioselective Synthesis of Sulfur-Containing N-Alkyl Carbamates from Alkyne-Derived Cyclic Carbonates

doi:10.21127/yaoyigc20180007

Abstract

Abstract: 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.

Key words: organocatalyst, sulfur-containing N-alkyl carbamate, tri-substituted cyclic carbonate, regioselective ring-opening, 1,5,7-triazabicyclo[4.4.0]dec-5-ene

Bin Liu, Xinghong Zhang. Organocatalytic Regioselective Synthesis of Sulfur-Containing N-Alkyl Carbamates from Alkyne-Derived Cyclic Carbonates[J]. General Chemistry, 2018, 4(3): 180007-180007.

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