Tertiary Amides as Fluoroalkyl Aldehyde Surrogates: Access to meso-Fluorinated Bis(heteroaryl)methanes

Tertiary, morpholine-derived, fluoroalkyl amides have been found to be efficient, readily accessible, bench-stable surrogates of fluoroalkyl aldehydes. This discovery is applied to the one-pot synthesis of a symmetrical and, more challengingly, unsymmetrical meso-fluoroalkylated bis(heteroaryl)methanes via a Schwartz's reagent-mediated reductive activation. The usefulness of this approach for the introduction of a fluoromethylated carbon bridge was proven by implementation of the developed methodology in the synthesis of a fluorine-decorated bispyrromethane skeleton and an α-alkylated BODIPY core.