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Published on: August 17, 2018
Highly Efficient Conversion of Propargylic Alcohols and Propargylic Amines with CO2 Activated by Noble-Metal-Free
Ai-Ling Gu1,2, Ya-Xin Zhang1,2, Zhi-Lei Wu1,2
1Department of Chemistry, Key Laboratory of Advanced Energy Material Chemistry, MOE, Renewable Energy Conversion and Storage Center (RECAST), Nankai University, Tianjin, 300071, China.
Abstract:
The cyclization reactions of propargylic alcohols and propargylic amines with CO2 are important in industrial applications, but it was a great challenge that non-noble-metal catalysts catalyzed both reactions under mild conditions. Herein, the catalyst Cu2 O@ZIF-8 was prepared by encapsulating Cu2 O nanoparticles into robust ZIF-8, and it can effectively catalyze the cyclization of both propargylic alcohols and propargylic amines with CO2 into valuable α-alkylidene cyclic carbonates and oxazolidinones with turnover numbers (TONs) of 12.1 and 19.6, which can be recycled at least five times. The mechanisms were further uncovered by NMR, FTIR, 13 C isotope-labeling experiments and DFT calculations, in which Cu2 O and DBU can synergistically activate the C≡C bond and the hydroxy/amino group of substrates. Importantly, it is the first example of a noble-metal-free catalyst that can catalyze both propargylic alcohols and propargylic amines with CO2 simultaneously.
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