Outer-Sphere Electrophilic Fluorination of Organometallic Complexes

Lucy M. Milner, Natalie E. Pridmore, Adrian C. Whitwood, Jason M. Lynam*, John M. Slattery

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

9 Citations (Scopus)

Abstract

Organofluorine chemistry plays a key role in materials science, pharmaceuticals, agrochemicals, and medical imaging. However, the formation of new carbon-fluorine bonds with controlled regiochemistry and functional group tolerance is synthetically challenging. The use of metal complexes to promote fluorination reactions is of great current interest, but even state-of-the-art approaches are limited in their substrate scope, often require activated substrates, or do not allow access to desirable functionality, such as alkenyl C(sp2)-F or chiral C(sp3)-F centers. Here, we report the formation of new alkenyl and alkyl C-F bonds in the coordination sphere of ruthenium via an unprecedented outer-sphere electrophilic fluorination mechanism. The organometallic species involved are derived from nonactivated substrates (pyridine and terminal alkynes), and C-F bond formation occurs with full regio- and diastereoselectivity. The fluorinated ligands that are formed are retained at the metal, which allows subsequent metal-mediated reactivity.

Original languageEnglish
Pages (from-to)10753-10759
Number of pages7
JournalJournal of the American Chemical Society
Volume137
Issue number33
DOIs
Publication statusPublished - 13 Aug 2015

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