A general illustration of the transition-metal catalyzed C–H activation of amidines for the synthesis of potential bioactive molecules.
Amidine compounds, as important nitrogen analogues of isoelectronic carboxylic acids, are found throughout biologically active molecules and serve as the most attractive precursors for the synthesis of N-containing compounds.
Amidines are a relatively unexplored single-atom isostere of the amide bond, offering unique electronic properties and hydrogen-bonding behavior.
Primary trifluoroborate-iminiums are transformed into N-sulfonyl amidines in an azide- and transition-metal-free C(sp2)–N bond-forming reaction under mild conditions. The mechanism was elucidated via NMR, mass spectrometry and DFT calculations.
Amidines are an isostere of the amide bond and are completely unexplored in peptide secondary structure.