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Molecules 2019, 24, 182 4 of 41 Molecules 2019, 24, x FOR PEER REVIEW 4 of 42 Gratifyingly, He et al. obtained corresponding 2-oxazolidinones in moderate to excellent yields Gratifyingly, He et al. obtained corresponding 2-oxazolidinones in moderate to excellent yields by using a bifunctional Ag WO /Ph P system (Scheme 3a and Figure 1) [21]. The reaction was carried 243 by using a bifunctional Ag2WO4/Ph3P system (Scheme 3a and Figure 1) [21]. The reaction was carried outunder0.5MPapressureofCO and50◦Cwithoutusinganysolvent.AsshowninScheme3a,the out under 0.5 MPa pressure of CO2 2 and 50 °C without using any solvent. As shown in Scheme 3a, the high catalytic activity was ascribed to the dual activation capacity of Ag WO . The silver ion, acting as high catalytic activity was ascribed to the dual activation capacity of A2g2WO44. The silver ion, acting a π-Lewis acid, could activate the C-C triple bond. Meanwhile, both CO and the O-H bond of the as a π-Lewis acid, could activate the C-C triple bond. Meanwhile, both CO2 and the O-H bond of the proppraorpgayrlgiyclaiclcaolchohlowlewreraecatcivtiavtaetdedbybytutunnggsstatateteaaniion.. OOOO nPr nBu Bn ONONONON 83% 92% 85% 93% OOO nBu nBu nBu ONONON Ph Et 95% 88% 89% Figure 1. Some 2-oxazolidinone derivatives by Ag WO /Ph P system (isolated yields are given) [21]. Figure 1. Some 2-oxazolidinone derivatives by Ag22WO4/Ph3P3 system (isolated yields are given) [21]. Recently, a noninterpenetrated primitive-cubic (pcu)-type sulfonate-based metal-organic Recently, a noninterpenetrated primitive-cubic (pcu)-type sulfonate-based metal-organic framework (MOF) was synthesized by Fei et al. [27]. Due to the unusual linker-defective nature framework (MOF) was synthesized by Fei et al. [27]. Due to the unusual linker-defective nature of oftheMOF,Ag(I)activesiteswereincorporated.ThesynergisticeffectofhighCO affinityandalkyne the MOF, Ag(I) active sites were incorporated. The synergistic effect of high CO2 a2ffinity and alkyne actaivcatitvioatnionnatunraeteunreablendaAblge(dI)-dAegc(oIr)-adtedcosrualtfeodnasteu-lMfoOnaFtes-uMccOeFssfusullcycceasstafulyllzye thcaetacylyczliec ctahreboxcylcalitcion ofpcarrobpoaxryglyaltiaolncohfoplrionptoarogxyalzaolcloidhionloinetosuonxadzeorliadtimnonspesheurnidceprreastmsuorsepohferCicOpriensstuhreeporfodCuOc2tiynietlhdeof 2 upptroo1d0u0c%ty(iSecldheomfeup3bt)o.N10o0t%ab(lSyc,haefmaset3mba).ssNtortanbslyp,oartfraesstumltainssgtfraonmsptohrethreigsuhltsiunrgfafrcoemartehaeahnidghthe robsusrtfancaetaureaoafntdhethpecruobtoupstonloagtuyrreeosuf tlht einpacuhitgophoclaotgaylyrteiscuelftfiincieanhciyg.h catalytic efficiency. An alternative catalyst to obtain 2-oxazolidinone derivatives or 2(3H)-oxazolones was a simple An alternative catalyst to obtain 2-oxazolidinone derivatives or 2(3H)-oxazolones was a simple 2.1.2. Synthesis of Carbamates 2.1.2. Synthesis of Carbamates ′ ′′ organocatalyst, i.e., 2,2′,2′′-terpyridine in the absence of any solvent (Scheme 3c) [18]. Nevertheless, organocatalyst,i.e.,2,2,2 -terpyridineintheabsenceofanysolvent(Scheme3c)[18].Nevertheless, high temperature and CO2 pressure was indispensable. Besides, this catalytic system was not high temperature and CO2 pressure was indispensable. Besides, this catalytic system was not suitable suitable for anilines or internal propargyl alcohols. for anilines or internal propargyl alcohols. One of the most important acyclic carbamates, i.e., β-oxopropylcarbamate, has attracted One of the most important acyclic carbamates, i.e., β-oxopropylcarbamate, has attracted increased increased attention owing to its growing applications in agriculture and pharmacology [28]. It also attention owing to its growing applications in agriculture and pharmacology [28]. It also acts as a acts as a useful intermediate in organic synthesis as well as an amine protective group in peptide useful intermediate in organic synthesis as well as an amine protective group in peptide chemistry [29]. chemistry [29]. A one-pot reaction of a propargylic alcohol, secondary amine and CO2 is an A one-pot reaction of a propargylic alcohol, secondary amine and CO2 is an environmentally benign environmentally benign strategy to produce β-oxopropylcarbamate with high atom economy and strategy to produce β-oxopropylcarbamate with high atom economy and easy handling [19]. Unlike easy handling [19]. Unlike the formation of 2-oxazolidinone derivatives, β-oxopropylcarbamates can the formation of 2-oxazolidinone derivatives, β-oxopropylcarbamates can be obtained via nucleophilic be obtained via nucleophilic ring-opening of α-alkylidene cyclic carbonates and subsequent ring-opening of α-alkylidene cyclic carbonates and subsequent tautomerization (See Scheme 2, tautomerization (See Scheme 2, Path B) [21]. Path B) [21]. There are various well-established protocols with metal complexes including ruthenium(II) There are various well-established protocols with metal complexes including ruthenium(II) [30], [30], iron complexes based on 1,1′-bis(diphenylphosphino)-ferrocene [31] and silver complexes [29] iron complexes based on 1,1′-bis(diphenylphosphino)-ferrocene [31] and silver complexes [29] etc. etc. that were developed before 2012. Additionally, bicyclic guanidines [24] and noncatalytic that were developed before 2012. Additionally, bicyclic guanidines [24] and noncatalytic systems [28] systems [28] were also demonstrated effective in the coupling of propargylic alcohols, secondary were also demonstrated effective in the coupling of propargylic alcohols, secondary amines and CO . amines and CO2. Unfortunately, these approaches generally have severe limitations such as high 2 Unpforertsusunraete(l≥y2, tMhePsae) apndpraodadchiteiosngaelneenrearlgly hreaqvueisremveernetlsi.mitations such as high pressure (≥2 MPa) and additionInalrecnenrtgyeraerqsu,isrielvmere-nctosn.tainingcatalyticsystemshaveshowedexcellentperformanceinthe prIondurecctieontoyfeβa-rosx,ospilrvoepry-clcoanrbtaimniantegsctahtraoluygtihctshyesthemrees-hcoamveposnheonwteredaectxicoenlsl,eanstspheorwfonrminaTnacbelein1.the production of β-oxopropylcarbamates through the three-component reactions, as shown in Table 1.PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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