Sustainable and Chemoselective Synthesis of α-Aminonitriles Using Lewis and Brønsted Acid-Functionalized Nanoconfined Spaces
01 natural sciences
0104 chemical sciences
DOI:
10.1021/acsami.2c13945
Publication Date:
2022-10-27T08:50:24Z
AUTHORS (5)
ABSTRACT
α-Aminonitriles are significant components in the synthesis of biological compounds and complex drugs. Although efficient, procedures for synthesizing α-aminonitriles suffer from high loadings of expensive catalysts, long reaction times, energy-intensive conditions, and expensive, toxic solvents. Herein, we report the use of metal-organic framework Cr-MIL-101-SO3H as a catalyst for the facile synthesis of eight α-aminonitriles, five of which are reported as new molecules. We found that the presence of both open Cr3+ Lewis and -SO3H Brønsted acids in the MIL-101 pores is vital for the one-pot synthesis of α-aminonitriles. The catalytic reaction is conducted under solvent-free conditions at room temperature and a Cr-MIL-101-SO3H loading of 1% by the total mass, which is considered a sustainable synthetic pathway of α-aminonitriles. Additionally, we demonstrated for the first time that Cr-MIL-101-SO3H exhibits a high degree of catalytic chemoselectivity, differing substrates with sterically hindered and electronically withdrawn functional groups. Our study expands the existing family of α-aminonitriles and provides an intelligent strategy for the development of catalysts that can be used to synthesize functional α-aminonitriles with potential in therapeutics and health applications.
SUPPLEMENTAL MATERIAL
Coming soon ....
REFERENCES (26)
CITATIONS (7)
EXTERNAL LINKS
PlumX Metrics
RECOMMENDATIONS
FAIR ASSESSMENT
Coming soon ....
JUPYTER LAB
Coming soon ....