Dosage Delivery of Sensitive Reagents Enables Glove Box-Free Synthesis

Contemporary organic chemists employ a broad range of catalytic and stoichiometric methods to construct molecules for applications in many fields, including material sciences(1), pharmaceuticals(2–5), agrochemicals, and sensors(6). The potential utility of a synthetic method can be greatly reduced if it relies on the use of air- and/or moisture-sensitive reagents or catalysts. Furthermore, many synthetic chemistry laboratories have numerous containers of partially used reagents that have been spoiled by exposure to the ambient atmosphere. This is exceptionally wasteful from both an environmental and a cost perspective. In this manuscript, we report an encapsulation method through which air- and moisture-sensitive sensitive compounds can be rendered stable and stored on a laboratory bench top. We demonstrate this approach in three contexts, by describing single use capsules that contain all of the reagents (i.e., catalysts, ligands, and bases) necessary for palladium-catalyzed carbon–fluorine(7–9), carbon–nitrogen(10,11), and carbon–carbon(12) bond forming reactions. The strategy described in this paper should be broadly applicable to a wide range of reagents and catalysts and should have the power to be transformative in preparative organic chemistry, particularly for inexperienced chemists. In addition, this approach will reduce the amount of tedious and time-consuming weighing procedures for the synthetic chemist performing these techniques on a large number of substrate combinations.