Defluorinative Coupling of (NH)-Heteroarenes and Unactivated Vinyl Fluorides Enabled by Metal-Organic Frameworks.

ABSTRACT: N-vinyl azoles are prevalent moieties in pharmaceuticals, and fluorovinyl groups are widely recognized as carbonyl bioisosteres in drug design. Thus, N-fluorovinylated heteroarenes represent highly desirable functional groups in medicinal chemistry. To streamline the development of novel N-fluorovinylation and N-pentafluoropropenylation reactions, herein we safely handle fluorinated gases, such as vinylidene fluoride (VDF) and hexafluoropropene (HFP), as solid reagents using a metal-organic framework (MOF), Mg₂(dobdc) (dobdc^4- = 2,5-dioxidobenzene-1,4-dicarboxylate). We report for the first time that free (NH)-heteroarenes─including various complex, biologically active molecules, react directly with VDF via a defluorinative pathway under mi

SUBMITTER: Keasler KT 

PROVIDER: S-EPMC12435398 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature