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Catalysts 2020, 10, 762 3 of 15 Catalysts 2020, 10, x FOR PEER REVIEW 3 of 16 (i) the ability of catalysts and ILs to recycle, (ii) product separation simplicity, (iii) the high productivity Canatdalystasb20i2li0t,y10o,fxtFhOeRsPyEsEteRmREs.VIEW 3of16 Scheme 1. Ionic liquids-based recyclable protocols for the synthesis of unsaturated organoboron compounds. ScheSmchee1m. eIon1.icIolinqiucidlisq-buaidsesd-braesceydclraebclyecplarbolteocporlsotfocrotlhsefsoyrnthessisynotfhuensissatoufrautnedsaoturgratneodborognancomboprounnds. compounds. 2. Results and Discussion 2. Results and Discussion 2. Results and Discussion 2.1. Reaction and Extraction Conditions Screening 2.1. RTehacetisotnudaniedsEwxterraectinonitiCatoendibtiyonasnSicinreveensitnigation of the borylative coupling of vinylboronic acid pinacolesetsetrer(1)(1w)itwhistthyresntyer(e2nae)a(s2a)maosdealrmeaoctdioelnprearfcotiromnedpienrfsoervmereadlILinsbsaesveedraolnIpLysrrbolaisdeidniuomn The studies were initiated by an investigation of the borylative coupling of vinylboronic acid ++ ++ (p[yErMroPliydri]ni)uomr 1([-EbMutPyyl-r3]-m) oerth1y-bliumtyidl-a3z-molieuthmyl(i[mBMidaImzo]liu) mcat(i[oBnMs Iamnd] )vcartiouns iannodrgvaanricouasndinorganic pinacol ester (1) with styrene (2a) as a model reaction performed in several ILs based on andionosr(gFaingiucrea1n)i.onMso(sFtiogfurtheem1).wMeroesstucocfestshfuemlly awpeprleiedsuicnceTsMsfu-clalytalyapzepdlietdranisnforTmMa-tciaotnasly[z1e6d]. pyrrolidinium ([EMPyr]+) or 1-butyl-3-methylimidazolium ([BMIm]+) cations and various inorganic Btroarnyslfaotrimveatciounpsl[i1n6g].iBs oarycalatatilvyeticoruepalcitniogniswahciacthaloycticcuresaicntitohnewphreicshenocecuorfsRinu-tHhecparteaslyenstcsewofitRhut-hHe and organic anions (Figure 1). Most of them were successfully applied in TM-catalyzed acactaivlyastitosnwoitfhththeeCa–cBtibvoatniodninofvtihneylCb–oBrobnoantdesinanvdintyhlebCo–roHnabtoensdanindothleefiCn–sHorbOo–nHd ibnoonldefinsaolcroOho–lHs, transformations [16]. Borylative coupling is a catalytic reaction which occurs in the presence of Ru-H sbiolanndolisnorablcoorhoonlisc,acsidlasnfoulrsniosrhinbgorboonriycl-asucibdsstitfutrendisohleinfignsb, booryrol-nsiucbestietrust,ebdoroalseifloinxsa,nbesoorornbiocroexsatenress, catalysts with the activation of the C–B bond in vinyl boronates and the C–H bond in olefins or O–H rbeosrpaesciltoivxealnye, swoitrhbtohreoxsiamneusltraensepoeucstiveveloyl,uwtioitnhothf etshiymleunltean[2e9o,4u0s–e4v3o].lution of ethylene [29,40–43]. bond in alcohols, silanols or boronic acids furnishing boryl-substituted olefins, boronic esters, borasiloxanes or boroxanes respectively, with the simultaneous evolution of ethylene [29,40–43]. Figure 1.. Mooddeell rreaccttiion off 1 with 2a used ffoorr ththeecoconndditiitoionnssscsrcereenniningg. . Pyrrolidinium and imidazolium-based ionic liquids used as solvents and catalyst immobilization mediia.. Figure 1. Model reaction of 1 with 2a used for the conditions screening. Pyrrolidinium and imidazolium-based ionic liquids used as solvents and catalyst immobilization media. For the initial ionic liquids screening, we applied slightly more rigorous reaction conditions if For the initial ionic liquids screening, we applied slightly more rigorous reaction conditions if compared to the traditional approach of utilizing volatile organic solvents (a higher process temperature compared to the traditional approach of utilizing volatile organic solvents (a higher process For the initial ionic liquids screening, we applied slightly more rigorous reaction conditions if to ensure good homogeneity of the reaction mixture). [Ru(CO)Cl(H)(PCy ) ] was used as a catalyst, temperature to ensure good homogeneity of the reaction mixture). [Ru(C3O2)Cl(H)(PCy3)2] was used compared to the traditional approach of utilizing volatile organic solvents (a higher process which was previously described as the most effective in this transformation. In all pyrrolidinium-based as a catalyst, which was previously described as the most effective in this transformation. In all temperature to ensure good homogeneity of the reaction mixture). [Ru(CO)Cl(H)(PCy3)2] was used ionic liquids, a conversion of 1 was over 90% (Table 1, entry 1–4). The complete conversion of 1 was pyrrolidinium-based ionic liquids, a conversion of 1 was over 90% (Table 1, entry 1–4). The complete as a catalyst, which was previously described as the most effective in this transformation. In all observed only for [EMPyr][NTf ]. In general, a higher conversion of 1 was observed for pyrrolidinium conversion of 1 was observed2 only for [EMPyr][NTf2]. In general, a higher conversion of 1 was pyrrolidinium-based ionic liquids, a conversion of 1 was over 90% (Table 1, entry 1–4). The complete cations with ethyl substituents. When butyl groups were attached to the pyrrolidinium cation, observed for pyrrolidinium cations with ethyl substituents. When butyl groups were attached to the conversion of 1 was observed only for [EMPyr][NTf2]. In general, a higher conversion of 1 was pyrrolidinium cation, the product yield was slightly lower. Simultaneously, the application of observed for pyrrolidinium cations with ethyl substituents. When butyl groups were attached to the trifluoromethanesulfonate anion ([OTf]−) resulted in the lower conversion of substrates than for pyrrolidinium cation, the product yield was slightly lower. Simultaneously, the application of bis(trifluoromethylsulfonyl)imide anion ([NTf2]−). trifluoromethanesulfonate anion ([OTf]−) resulted in the lower conversion of substrates than for bis(trifluoromethylsulfonyl)imide anion ([NTf2]−).PDF Image | Ru-Catalyzed Repetitive Batch Borylative Coupling of Olefins
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