TBD catalysis with dimethyl carbonate: A fruitful and sustainable alliance

Abstract

This work presents the synthesis of unsymmetric and symmetric organic carbonates as well as the synthesis of polycarbonates in an efficient and sustainable approach. All reactions were carried out at atmospheric pressure at 80 °C and the use of classic toxic and harmful chemicals, such as phosgene and carbon monoxide, was avoided. The key finding of this manuscript is that the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, an organocatalyst, in combination with dimethyl carbonate (DMC), a non-toxic and renewable starting material, allows the synthesis of the mentioned unsymmetric carbonates in yields of up to 98% under optimized conditions. The structure of the alcohols used for this approach was found to influence the DMC–ROH ratio required to maximize the yield of the desired structure. Finally, the results obtained for the synthesis of low molecular weight building blocks could be transferred to the catalytic synthesis of high molecular weight polycarbonates. © 2012 The Royal Society of Chemistry.