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Catalysts 2020, 10, x FOR PEER REVIEW 9 of 16 extraction (160–180 bar of CO2 at 40 °C, 8 mL/min, 45 min) conditions. Visualization of the reaction mixture through the sapphire window of high-pressure autoclave’s (d). The product yields were Catalysts 2020, 10, 762 9 of 15 determined by GC-MS. The extraction yields refer to the mass of products and reactants. For 4-(triflfluoromethyl)styrene (2d) and vinylcyclohexane (2j), very high reaction and extraction yieldsofprroduccttsswwereereobosbesrevrevdeduputpotohethsiextshixrtuhnr,uwnh,ewrehueproenupaognraadugaralduecarledaseecrinearseeacintiorneayciteilodns ywiealsdnsowticaesd.nEoxtticraecdt.ionEyxietrladcstiroenmayiineeldsatreamvearinyehdigaht leavevlerreygahrdiglhessleovfetlhererguanr.dAledsds itoiof ntahlely,rtuhne. Anedgdlitgioibnlaellya,mthoeunetgloigfibmleeatamloiunntaollfmanetaallyiznedalleaxntarlaycztesd(e0x.8tr8a–c0t.s5(40.8p8p–m0.)54cplepamrl)yclesuarglgyesutegdgesttheadt t[hRaut(C[ROu)C(Cl(OH))C(Pl(CHy)3()P2]Cwya)s s]trwonasglystrimonmgolybiilimzemdoibnil[iBzMedImin][O[BTMf]Iumn]d[eOrTafp]pulinedereacptipolniecdonrdeaitcitoinosn. 32 cTohnedistaiotinssfa. cTtohreysasttiasfbaiclitoyryasntdabailcityivaitnydoafcttivhiety[Rofut(hCeO[)RCul(CHO)()PCly(H3))2](@PC[ByM)Im]@][OBMTfI]m/s]c[COOT2f]/ssycsCteOm 322 scyresatetmescarneaotepspaonrtoupnpitoyrtfuonriittysfaoprpitlsicaptipolnicaintiocnonintincounotuins-uflouws-flbowrylbaotirvyelactiovuepcloinugplrienagctrieoancstioinsthine tfhuetufruet.ure. At the end of our investigation on repetitive batch borylative coupling in the biphasic system, we verifified the possibility of direct use of extracts in deborylation protocols, i.e., Suzuki coupling and iododeborylation (Scheme 2). Scheme 2. Transformations of 3a via Suzuki coupling and iododeborylation reactions. Scheme 2. Transformations of 3a via Suzuki coupling and iododeborylation reactions. Suzuki coupling of 3a with bromobenzene in the presence of [Pd(PPh3)4] occurred with a Suzuki coupling of 3a with bromobenzene in the presence of [Pd(PPh3)4] occurred with a complete conversion of 3a and with a very high isolation yield of (E)-1,2-diphenylethene (4) (87%). complete conversion of 3a and with a very high isolation yield of (E)-1,2-diphenylethene (4) (87%). Similarly, iododeborylation of 3a with molecular iodine in the presence of sodium hydroxide resulted Similarly, iododeborylation of 3a with molecular iodine in the presence of sodium hydroxide resulted in a high isolation yield of (E)-(2-iodovinyl)benzene (5) (81%). The possibility of applying deborylation in a high isolation yield of (E)-(2-iodovinyl)benzene (5) (81%). The possibility of applying protocols with the use of crude extract is an attractive approach from the synthetical point of view deborylation protocols with the use of crude extract is an attractive approach from the synthetical because of the lack of necessity of carrying out time- and cost-consuming purification steps, for example, point of view because of the lack of necessity of carrying out time- and cost-consuming purification column chromatography or distillation. steps, for example, column chromatography or distillation. 3. Materials and Methods 3. Materials and Methods 3.1. Materials 3.1. Materials Vinylboronic acid pinacol ester (95%, Sigma-Aldrich), styrene (97%, Sigma-Aldrich, Poznan ́ , Poland), Vinylboronic acid pinacol ester (95%, Sigma-Aldrich), styrene (97%, Sigma-Aldrich, Poznań, 4-bromostyrene (97%, Sigma-Aldrich), 4-fluorostyrene (99%, Sigma-Aldrich), 4-(trifluoromethyl)styrene Poland), 4-bromostyrene (97%, Sigma-Aldrich), 4-fluorostyrene (99%, Sigma-Aldrich), 4- (98%, Sigma-Aldrich), 3,5-bis(trifluoromethyl)styrene (98%, Alfa Aesar, Kandel, Germany), (trifluoromethyl)styrene (98%, Sigma-Aldrich), 3,5-bis(trifluoromethyl)styrene (98%, Alfa Aesar, 4-methylstyrene (96%, Sigma-Aldrich), 2-methylstyrene (95%, Sigma-Aldrich), 4-t-butylstyrene (93%, Kandel, Germany), 4-methylstyrene (96%, Sigma-Aldrich), 2-methylstyrene (95%, Sigma-Aldrich), 4- Sigma-Aldrich), 4-methoxystyrene (97%, Sigma-Aldrich), vinylcyclohexane (99%, Sigma-Aldrich) were t-butylstyrene (93%, Sigma-Aldrich), 4-methoxystyrene (97%, Sigma-Aldrich), vinylcyclohexane applied as reagents in borylative coupling reactions. Sodium hydroxide (99%, POCH Basic, Gliwice, (99%, Sigma-Aldrich) were applied as reagents in borylative coupling reactions. Sodium hydroxide Poland), iodine (99.8%, Sigma-Aldrich), diethyl ether (99%, POCH Basic), potassium carbonate (99%, (99%, POCH Basic, Gliwice, Poland), iodine (99.8%, Sigma-Aldrich), diethyl ether (99%, POCH Basic), Sigma-Aldrich), bromobenzene (99%, Sigma-Aldrich), tetrakis (triphenylphosphine)palladium (0) (99%, potassium carbonate (99%, Sigma-Aldrich), bromobenzene (99%, Sigma-Aldrich), tetrakis Sigma-Aldrich) were applied as received. 1-Ethyl-1-methylpyrrolidinium trifluoromethanesulfonate (triphenylphosphine)palladium (0) (99%, Sigma-Aldrich) were applied as received. 1-Ethyl-1- (99%, IoLiTec, Heilbronn, Germany), 1-ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide methylpyrrolidinium trifluoromethanesulfonate (99%, IoLiTec, Heilbronn, Germany), 1-ethyl-1- (98%, Sigma-Aldrich), 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate (95%, Sigma-Aldrich), methylpyrrolidinium bis(trifluoromethylsulfonyl)imide (98%, Sigma-Aldrich), 1-butyl-1- 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide (98%, Sigma-Aldrich), 1-butyl-3- methylpyrrolidinium trifluoromethanesulfonate (95%, Sigma-Aldrich), 1-butyl-1- methylimidazolium bis(trifluoromethylsulfonyl)imide (98%, Sigma-Aldrich), 1-butyl-3- methylpyrrolidinium bis(trifluoromethylsulfonyl)imide (98%, Sigma-Aldrich), 1-butyl-3- methylimidazolium trifluoromethanesulfonate (97%, Sigma-Aldrich), 1-butyl-3-methylimidazolium methylimidazolium bis(trifluoromethylsulfonyl)imide (98%, Sigma-Aldrich), 1-butyl-3- hexafluorophosphate (97%, Sigma-Aldrich), 1-butyl-3-methylimidazolium tetrafluoroborate (98%, methylimidazolium trifluoromethanesulfonate (97%, Sigma-Aldrich), 1-butyl-3-methylimidazolium Sigma-Aldrich), 1-butyl-3-methylimidazolium chloride (99%, Sigma-Aldrich) were dried in a vacuum hexafluorophos◦phate (97%, Sigma-Aldrich), 1-butyl-3-methylimidazolium tetrafluoroborate (98%, before use (70 C, 18 h). Styrene, 4-methoxystyrene, and 4-tert-butylstyrene were purified by the Sigma-Aldrich), 1-butyl-3-methylimidazolium chloride (99%, Sigma-Aldrich) were dried in a bulb to bulb distillation before use. The carbon dioxide (99.995%, Messer Polska, Chorzów, Poland) vacuum before use (70 °C, 18 h). Styrene, 4-methoxystyrene, and 4-tert-butylstyrene were purified by was used as a solvent and extractant in the reactions carried out in scCO2. The ruthenium catalysts [Ru(CO)Cl(H)(PCy3)2] [45] and [Ru(CO)Cl(H)(PPh3)3] [46] were prepared according to literature procedures. Deuterium solvents were obtained from Dr. Glaser AG Basel. The n-hexane (99%, POCHPDF Image | Ru-Catalyzed Repetitive Batch Borylative Coupling of Olefins
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