Handling fluorinated gases as solid reagents using metal-organic frameworks

Fluorine is an increasingly common substituent in pharmaceuticals and agrochemicals because it improves the bioavailability and metabolic stability of organic molecules. Fluorinated gases represent intuitive building blocks for the late-stage installation of fluorinated groups, but they are generall...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2023-09, Vol.381 (6665), p.1455-1461
Main Authors: Keasler, Kaitlyn T, Zick, Mary E, Stacy, Emily E, Kim, Jaehwan, Lee, Jung-Hoon, Aeindartehran, Lida, Runčevski, Tomče, Milner, Phillip J
Format: Article
Language:English
Subjects:
Fluorination
Fluorocarbons
Gases
Magnesium
Metal-organic frameworks
Reagents
Sonication
Styrene
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Summary:Fluorine is an increasingly common substituent in pharmaceuticals and agrochemicals because it improves the bioavailability and metabolic stability of organic molecules. Fluorinated gases represent intuitive building blocks for the late-stage installation of fluorinated groups, but they are generally overlooked because they require the use of specialized equipment. We report a general strategy for handling fluorinated gases as benchtop-stable solid reagents using metal-organic frameworks (MOFs). Gas-MOF reagents are prepared on gram-scale and used to facilitate fluorovinylation and fluoroalkylation reactions. Encapsulation of gas-MOF reagents within wax enables stable storage on the benchtop and controlled release into solution upon sonication, which represents a safer alternative to handling the gas directly. Furthermore, our approach enables high-throughput reaction development with these gases.
ISSN:0036-8075
1095-9203
1095-9203
DOI:10.1126/science.adg8835