Base‐Mediated Remote Deuteration of <i>N</i> ‐Heteroarenes – Broad Scope and Mechanism

Deuterated organic molecules provide the basis for many applications in life sciences and material research. Thus, methodologies to access labeled compounds with defined selectivity continue be important. Using KOtBu as base DMSO-d6 deuterium source, we present a general applicable method selective deuteration of set nitrogen-containing heterocycles (pyridines, azines bioactive molecules). Experimental DFT mechanistic studies indicate that this reaction proceeds via deprotonation substrates by dimsyl anion. The relative thermodynamic stability heterocycle anions determines distribution degree deuteration.