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The rapid access to isotopically labeled organic molecules is a sine qua non condition to support these societally vital areas of research. Based on a rationally driven approach, this study presents an innovative solution to access labeled pyridines by a nitrogen isotope exchange reaction based on a Zincke activation strategy. The technology conceptualizes an opportunity in the field of isotope labeling. <jats:sup>15<\/jats:sup>N-labeling of pyridines and other relevant heterocycles such as pyrimidines and isoquinolines showcases on a large set of derivatives, including pharmaceuticals. Finally, we explore a nitrogen-to-carbon exchange strategy in order to access <jats:sup>13<\/jats:sup>C-labeled phenyl derivatives and deuterium labeling of mono-substituted benzene from pyridine-<jats:sup>2<\/jats:sup>H<jats:sub>5<\/jats:sub>. 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