We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [(18)F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.

Through fine-tuning of reagent and base structure, sulfonyl fluorides can efficiently fluorinate diverse classes of alcohols. We show that machine learning can map the intricate reaction landscape and enable accurate prediction of high-yielding conditions for untested substrates.

We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane via nickel and photoredox catalysis. This scalable, benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. Mild conditions enable unprecedented scope from abundant and complex aryl chloride starting materials.

The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules.

We report ar edox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis.This scalable benchtop approach provides adistinct advantage over traditional reductive carbonylation in that no carbon monoxide,pressurized gas,orstoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.