Tertiary Amides as Fluoroalkyl Aldehyde Surrogates: Access to -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 -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.

Reductive Functionalization of Amides in Synthesis and for Modification of Bioactive Compounds.

In this review, applications of the amide reductive functionalization methodology for the synthesis and modification of bioactive compounds are covered. A brief summary of the different protocols is presented in the introduction, followed by the synthetic application of these in late-stage functionalization, leading to known pharmaceuticals or to their derivatives, including bioisosteres, with potential higher activity as the main axis of the article. The synthetic approach to natural products based on amide reduction is also discussed; however, this is given in a condensed form focusing on recent or as yet unexplored applications due to a number of recently published excellent reviews covering this topic.

Overcoming inaccessibility of fluorinated imines - synthesis of functionalized amines from readily available fluoroacetamides.

Although imines are convenient substrates for the synthesis of functionalized amines, they may be hard to obtain, as in the case of fluorinated imines. To aid in overcoming this issue, we propose a protocol of corresponding amine synthesis from simple fluoroacetic acid-derived amides using Schwartz's reagent.