Exploration of Mechanochemical Activation in Solid-State Fluoro-Grignard Reactions.

ABSTRACT: Owing to the strength of the C-F bond, the 'direct' preparation of Grignard reagents, i.e., the interaction of elemental magnesium with an organic halide, typically in an ethereal solvent, fails for bulk magnesium and organofluorine compounds. Previously described mechanochemical methods for preparing Grignard reagents have involved ball milling powdered magnesium with organochlorines or bromines. Activation of the C-F bond through a similar route is also possible, however. For example, milling 1- and 2-fluoronaphthalene with an excess of magnesium metal for 2 h, followed by treatment with FeCl₃ and additional milling, produces the corresponding binaphthalenes, albeit in low yields (ca. 20%). The yields are independent of the particular isomer involved and are also comparable to

SUBMITTER: Speight IR 

PROVIDER: S-EPMC7037680 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature