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extraction. Simultaneously, the efficiency of extraction for different products of 3 was investigated. n- Heptane (3 × 5 mL at 60 °C) or scCO2 (160–180 bar of CO2 at 40 °C, 8 mL/min, 45 min) were applied as extractants. Very high extraction yields (over 90%) using n-heptane were obtained for most of the Catalysts 2020, 10, 762 7 of 15 products (3a–f, 3j). Similar results were achieved for the product extraction with scCO2. It is worth noticing that when CO2-philic groups such as –F or –CF3 were attached to the phenyl rings (3c–e), the extraScitmiounltyaineledosuisnlys,cthCeOe2ffiwceierencsyligohf etlxytrhaicgthioenr f(oTradbilffee4r,eennttpryro3d–u5c)t.sTohfe3ewxtarsaicntivoenstoigfaptreodd. unc-Ht 3ejpwtainthe ◦◦ (a3c×yc5lomhLexayt6l0rinCg)worascaClmOos(1t6q0u–a1n8t0itbaatrivoefdCuOetaoti4t0sgCoo,8dmafLfi/nmiitny,t4o5bmoitnh)ewxteraecatapnptlsie.dasextractants. 22 Very high extraction yields (over 90%) using n-heptane were obtained for most of the products (3a–f, 3j). S2.i3m.iRlaerperteitsiuvletsBawtcehreBaocryhliaetviveedCfourptlhinegpirnotdhuecMteoxntorpahcatsioicnSwolivtehnstcSCyOstem.I—ti[sRwu(oCrOth)Cnlo(tHic)i(nPgCyth3)a2]t@wILhsen 2 CO2-philic groups such as –F or –CF3 were attached to the phenyl rings (3c–e), the extraction yields in A key objective of our research was to develop an efficient and more sustainable protocol for the scCO2 were slightly higher (Table 4, entry 3–5). The extraction of product 3j with a cyclohexyl ring synthesis of (E)-alkenyl boronates via borylative coupling of vinyl boronates with olefins in ILs. was almost quantitative due to its good affinity to both extractants. Having optimized the process (reaction and extraction) conditions, as well as the information on the reactivity of olefins (2a–j), we verified the possibility of catalytic system recycling after each run using 2.3. Repetitive Batch Borylative Coupling in the Monophasic Solvent System—[Ru(CO)Cl(H)(PCy3)2]@ILs [BMIm][OTf] and [EMPyr][NTf2] as solvents. For repetitive batch borylative coupling of 1 with A key objective of our research was to develop an efficient and more sustainable protocol for the olefins, 2a, and 2d were chosen as reagents due to their excellent reaction and extraction yields. Trans- synthesis of (E)-alkenyl boronates via borylative coupling of vinyl boronates with olefins in ILs. Having borylation of 1 with 2a in [BMIm][OTf] and [EMPyr][NTf2] (Figure 2a,b) gave a final product 3a with optimized the process (reaction and extraction) conditions, as well as the information on the reactivity of very high yields up to the sixth run. For both ionic liquids, a gradual decrease in the reaction yield in olefins (2a–j), we verified the possibility of catalytic system recycling after each run using [BMIm][OTf] the seventh up to the 10th cycle was observed. A higher extraction yield for extractant-soluble and [EMPyr][NTf ] as solvents. For repetitive batch borylative coupling of 1 with olefins, 2a, and 2d 2 components (3a and excess or unreacted substrate) was noticed when n-heptane was used. Moreover, were chosen as reagents due to their excellent reaction and extraction yields. Trans-borylation of 1 with the cumulative turnover number (cTON) was several times higher than in the classical approach, 2a in [BMIm][OTf] and [EMPyr][NTf ] (Figure 2a,b) gave a final product 3a with very high yields up 2 utilizing volatile organic solvents (930–948 vs. approx. 50–100). to the sixth run. For both ionic liquids, a gradual decrease in the reaction yield in the seventh up to the Repetitive batch borylative coupling of 1 with 2d containing a CO2-phlilic trifluoromethyl group 10th cycle was observed. A higher extraction yield for extractant-soluble components (3a and excess gave a very high product yield (over 90%) up to the seventh cycle for [BMIm][OTf] and or unreacted substrate) was noticed when n-heptane was used. Moreover, the cumulative turnover [EMPyr][NTf2] (Figure 2c,d), respectively). The last three cycles resulted in a slight decrease in the number (cTON) was several times higher than in the classical approach, utilizing volatile organic reaction efficiency, but it was still at an acceptable level. Nevertheless, high values of cTON were solvents (930–948 vs. approx. 50–100). obtained (941–956), showing good system activity. Figure 2. Repetitive batch borylative coupling of 1 with 2a in [BMIm][OTf] (a) and [EMPyr][NTf2] (b) Figure 2. Repetitive batch borylative coupling of 1 with 2a in [BMIm][OTf] (a) and [EMPyr][NTf2] (b) or 1 with 2d in [BMIm][OTf] (c) and [EMPyr][NTf2] (d) under optimized reaction ([Ru-H]:1:2a or or 1 with 2d in [BMIm][OTf] (c) and [EMPyr][NTf2] (d) under optimized reaction ([Ru-H]:1:2a or 2d = 2d = 0.01:1:1.5, 110 ◦C, 6 h, 1 g of IL, inert atmosphere conditions) and extraction (3 × 5 mL of n-heptane 0.01:1:1.5, 110 °C, 6 h, 1 g of IL, inert atmosphere conditions) and extraction (3 × 5 mL of n-heptane at at 60 ◦C or 160–180 bar of CO2 at 40 ◦C, 8 mL/min, 45 min) conditions. The product yields were determined by GC-MS. The extraction yields refer to the mass of products and reactants. Repetitive batch borylative coupling of 1 with 2d containing a CO2-phlilic trifluoromethyl group gave a very high product yield (over 90%) up to the seventh cycle for [BMIm][OTf] and [EMPyr][NTf2] (Figure 2c,d), respectively). The last three cycles resulted in a slight decrease in the reaction efficiency,PDF Image | Ru-Catalyzed Repetitive Batch Borylative Coupling of Olefins
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