Search

The palladium-catalyzed C–H fluorination of 8-methylquinoline derivatives with nucleophilic fluoride is reported. This transformation involves the use of AgF as the fluoride source in combination with a hypervalent iodine oxidant. Both the scope and mechanism of the reaction are discussed.

This work provides a comprehensive review (1986–2010) of the synthesis, characterization, and reactivity of palladium(IV) complexes that undergo carbon–heteroatom bond-forming reductive elimination reactions. In cases where mechanistic information is available, the molecular pathway for C–X bond formation is described in detail. Examples of catalytic transformations that may involve this mechanistic manifold are also presented.

Pd(IV)-fluoride complexes, some of which are remarkably insensitive to water, have been synthesized and used in the title reaction, which proceeds with high selectivity to give the product of the C(sp(3))-F coupling. Preliminary mechanistic studies implicate a pathway involving dissociation of pyridine followed by direct C-F coupling at the Pd center.