Handling fluorinated gases as solid reagents using metal-organic frameworks

• 成果类型: Article
• 署名作者: Keasler, Kaitlyn T.; Zick, Mary E.; Stacy, Emily E.; Kim, Jaehwan; Lee, Jung-Hoon; Aeindartehran, Lida; Runcevski, Tomce; Milner, Phillip J.
• 署名单位: Cornell University; Korea Institute of Science & Technology (KIST); Southern Methodist University
• 刊物名称: SCIENCE
• ISSN/ISSBN: 0036-10450
• DOI: 10.1126/science.adg8835
• 发表日期: 2023-09-29
• 页码: 1455-1461
• 关键词: cross-coupling reactions; arylboronic acids; facile synthesis; adsorption; trifluoromethylation; functionalization; generation; SEPARATION; aldehydes; density

摘要

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.