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The selective synthesis of various dideuterochalcones as potentially bioactive deuterium‐labeled products is presented, by means of the highly controlled partial deuteration of antidiabetic chalcone derivatives. The benefits of continuous‐flow processing in combination with on‐demand electrolytic D2 gas generation has been exploited to avoid over‐reaction to undesired side products and to achieve selective deuterium addition to the carbon–carbon double bond of the starting enones without the need for unconventional catalysts or expensive special reagents. The roles of pressure, temperature, and residence time proved crucial for the fine‐tuning of the sensitive balance between the product selectivity and the reaction rate. The presented flow‐chemistry‐based deuteration technique lacks most of the drawbacks of the classical batch methods, and is convenient, time‐ and cost‐efficient, and safe.

Copper catalysed oxidative coupling reaction of formamides with β‐keto esters and 2‐carbonyl‐substituted phenols successfully proceeded through direct C–H bond activation of formamides. The corresponding carbamates were formed with high stereoselectivity under mild reaction conditions. This protocol was successfully applied to the synthesis of three novel halogenated carbamates and a carbaryl insecticide derivative. Our results suggest the use of 6.0 equiv. TBHP is crucial for this type of reaction.