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Emphasizing the intersection of chemical precision with drug discovery, the central challenge addressed is achieving one\u2010pot mono\u2010selective short\u2010chain N\u2010alkylations (methylations, ethylations, and\n                    <jats:italic>n<\/jats:italic>\n                    \u2010propylations), preventing undesired overalkylation. Additionally, sustainable, safe, and benign alternatives to traditional alkylating agents, including alcohols, carbon dioxide, carboxylic acids, nitriles, alkyl phosphates, quaternary ammonium salts, and alkyl carbonates, are explored. 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