Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 19, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202114817
Keywords
CO2; Metal-Organic Frameworks; Noble-Metal-Free; Propargylic Alcohols; Propargylic Amines
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Funding
- National Natural Science Foundation of China [21701039, 22121005, 21625103, 92161202]
- Hebei Natural Science Foundation [B2021201022]
- Priority Strategy Project of Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education [ts2020005]
- Project 111 [B12015]
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The Cu2O@ZIF-8 catalyst was prepared and demonstrated its effectiveness in catalyzing the cyclization reactions of propargylic alcohols and propargylic amines with CO2. This is the first noble-metal-free catalyst to simultaneously catalyze both reactions.
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 Cu2O@ZIF-8 was prepared by encapsulating Cu2O nanoparticles into robust ZIF-8, and it can effectively catalyze the cyclization of both propargylic alcohols and propargylic amines with CO2 into valuable alpha-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, C-13 isotope-labeling experiments and DFT calculations, in which Cu2O and DBU can synergistically activate the C equivalent to 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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