eCite Digital Repository

Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2

Citation

Cervantes-Reyes, A and Farshadfar, K and Rudolph, M and Rominger, F and Schaub, T and Ariafard, A and Hashmi, ASK, Copper-catalysed synthesis of alpha-alkylidene cyclic carbonates from propargylic alcohols and CO2, Green Chemistry, 23, (2) pp. 889-897. ISSN 1463-9262 (2021) [Refereed Article]

Copyright Statement

This journal is The Royal Society of Chemistry 2021

DOI: doi:10.1039/d0gc03990j

Abstract

We report a N-heterocyclic carbene copper(I) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demanding BPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylidene) and CsF, as catalytic system, primary propargylic alcohols are efficiently converted to the corresponding α-alkylidene cyclic carbonates. Gram scale (up to 89% yield) and reusability experiments (74% global yield, turnover number value = 103) showcase the robustness of the catalytic system. This practically simple protocol also tolerates secondary and tertiary propargylic alcohols under CO2 at atmospheric pressure, enabling the direct synthesis of substituted and unsubstituted α-alkylidene cyclic carbonates at room temperature.

Item Details

Item Type:Refereed Article
Keywords:copper catalysis, CO2 activation, DFT calculations
Research Division:Chemical Sciences
Research Group:Physical chemistry
Research Field:Catalysis and mechanisms of reactions
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:150048
Year Published:2021
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:8
Deposited By:College Office - CoSE
Deposited On:2022-05-16
Last Modified:2022-07-22
Downloads:0

Repository Staff Only: item control page