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2.6.1.3 Silver-Mediated Fluorination of Arylsilanes

DOI: 10.1055/sos-SD-208-00368

McMurtrey, K. B.; Sanford, M. S.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132555.

Trialkoxy(aryl)silanes 5 also participate in silver-mediated fluorination with Selectfluor (Scheme 3).[‌4‌] In this case, superstoichiometric silver(I) oxide (2 equiv relative to the silane) is used as the silver source. The addition of barium oxide (1.1 equiv) enhances the overall yields of products 6 by approximately 10%. The authors propose that this additive limits competing hydrodesilylation of the substrate. Importantly, unlike the analogous silver-mediated boronic acid fluorination (Section 2.6.1.2), this transformation can be performed in a single pot, as all of the reagents are mutually compatible. Otherwise, the substrate scope and reaction yields are similar to those observed with arylboronic acid substrates (Section 2.6.1.2).

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