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Catalysts 2020, 10, 762 5 of 15 Entry 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 d 16 17 18 19 20 d 21 Ionic Liquid Temperature Time [◦C] [h] 1:2a [mol] 1:4 1:4 1:4 1:4 1:4 1:4 1:4 1:3 1:2 1:2 1:1.5 1:1.5 1:1.5 1:1 1:1.5 1:1.5 1:1.5 1: 1.5 1:1 1: 1.5 1: 1.5 Catalyst Loading [mol%] 3 3 3 3 3 3 3 3 3 2 2 1 0.5 1 1 1 1 1 1 1 0.5 Conversion of 1 [%] a 100 100 96 88 100 100 94 100 100 100 100 100 93 100 46 100 53 91 100 41 89 Yield of 3a [%] b 100 100 96 88 100 100 94 100 100 100 100 100 93 83c 37e 100 53 91 88c 33e 89 Table 2. Reaction conditions screening for borylative coupling of 1 with 2a in the presence of immobilized [Ru(CO)Cl(H)(PCy3)2]@[EMPyr][NTf2] or @[BMIm][OTf]. [EMPyr][NTf2 ] 120 [EMPyr][NTf2 ] 110 24 [EMPyr][NTf2 ] 100 24 [EMPyr][NTf2 ] 80 24 [EMPyr][NTf2 ] 110 18 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 3 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2 ] 110 6 [EMPyr][NTf2] 110 6 [BMIm][OTf] 110 6 [BMIm][OTf] 80 6 [BMIm][OTf] 110 3 [BMIm][OTf] 110 6 [BMIm][OTf] 110 6 [BMIm][OTf] 110 6 a Determined by GC-MS analysis. b Determined by GC-MS and 1H NMR analyses. c Homocoupling of 1 was observed. d 1 mol% of [Ru(CO)Cl(H)(PPh3)3] was used as a catalyst. e Undefined side products were observed. Among many possibilities for the separation of products from the homogeneous reaction mixture, extraction seems to be a fast and efficient method. The extractant should dissolve the reaction products well, not mix with an ionic liquid to prevent leaching of the catalyst, as well as not inhibiting or deactivating the catalyst. The right choice is crucial for the ability to reuse the catalytic system. To find the most appropriate medium for product extraction, we examined several organic solvents and scCO2 (Table 3). Non-polar aliphatic hydrocarbons (n-hexane or n-heptane) are completely immiscible with [EMPyr][NTf2] and [BMIm][OTf], and during the extraction, the two phases were observed. The extractant (upper) phase was transparent or pale yellow. Application of more polar solvents such as toluene, dichloromethane or tetrahydrofuran resulted in partial or complete dissolution of the catalytic systems regardless of the ionic liquid used. Table 3. Extractant screening. Entry 1a 2a 3a 4b 5a 6c Solvent n-Hexane n-Heptane Toluene Dichloromethane Tetrahydrofuran Supercritical CO2 [EMPyr][NTf2 ] [BMIm][OTf] − − − − + + + + + + − − Extraction conditions: 3 × 5 mL of the solvent at a 60 or b 40 ◦C. c 160–180 bar of CO2 at 40 ◦C, 8 mL/min, 45 min). (−) Biphasic system. (+) Monophasic system or catalyst leaching from IL. Similar to aliphatic hydrocarbons, ScCO2 creates a biphasic solvent system with [EMPyr][NTf2] and [BMIm][OTf]. Additionally, it is known that scCO2 is partially soluble in ILs, lowering their viscosity, while ILs are not soluble in this supercritical fluid. Therefore, such a biphasic system is suitable for carrying out the reaction/extraction process [44]. Based on extractant screening for furtherPDF Image | Ru-Catalyzed Repetitive Batch Borylative Coupling of Olefins
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