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Molecules 2019, 24, 182 Molecules 2019, 24, x FOR PEER REVIEW 3 of 42 3 of 41 Molecules 2019, 24, x FOR PEER REVIEW 3 of 42 tedizolid [19]. Oxazolidinones can be prepared through the intramolecular nucleophilic cyclization tedizolid [19]. Oxazolidinones can be prepared through the intramolecular nucleophilic cyclization carbamates as well as chemical fixation of CO2 with several different reagents such as aziridines, of propynyl carbamates as well as chemical fixation of CO2 with several different reagents such as of propynyl carbamates as well as chemical fixation of CO2 with several different reagents such as aminoalcohols and propargylic amines [20]. However, from an availability and economic viability aziridines, aminoalcohols and propargylic amines [20]. However, from an availability and economic aziridines, aminoalcohols and propargylic amines [20]. However, from an availability and economic viewpoint, the three-component reaction of propargylic alcohols, primary amines and CO2 represents viability viewpoint, the three-component reaction of propargylic alcohols, primary amines and CO2 viability viewpoint, the three-component reaction of propargylic alcohols, primary amines and CO2 the most attractive method for the synthesis of oxazolidinone derivatives [19]. represents the most attractive method for the synthesis of oxazolidinone derivatives [19]. represents the most attractive method for the synthesis of oxazolidinone derivatives [19]. In the three-component reaction, the carboxylative cyclization of the propargyl alcohol with In the three-component reaction, the carboxylative cyclization of the propargyl alcohol with In the three-component reaction, the carboxylative cyclization of the propargyl alcohol with CO2 affords an α-alkylene cyclic carbonate, which then undergoes a nucleophilic attack by a CO2 affords an α-alkylene cyclic carbonate, which then undergoes a nucleophilic attack by a primary CO2 affords an α-alkylene cyclic carbonate, which then undergoes a nucleophilic attack by a primary primary amine followed by an intramolecular nucleophilic attack and dehydration to generate amine followed by an intramolecular nucleophilic attack and dehydration to generate amine followed by an intramolecular nucleophilic attack and dehydration to generate 4-alkylene-2-oxazolidinones or 2(3H)-oxazolones (See Scheme 2, Path A) [21]. It is worth noting 4-alkylene-2-oxazolidinones or 2(3H)-oxazolones (See Scheme 2, Path A) [21]. It is worth noting that 4-alkylene-2-oxazolidinones or 2(3H)-oxazolones (See Scheme 2, Path A) [21]. It is worth noting that that the formation of products is strongly associated with the substituents on the propargylic alcohols. the formation of products is strongly associated with the substituents on the propargylic alcohols. the formation of products is strongly associated with the substituents on the propargylic alcohols. Scheme 2. The mechanism for three-component reaction of propargylic alcohols, amines and CO Scheme 2. The mechanism for three-component reaction of propargylic alcohols, amines and CO2. 2. Scheme 2. The mechanism for three-component reaction of propargylic alcohols, amines and CO2. This reaction was catalyzed by copper salts including CuCl [22] and CuI [23], with the assistance This reaction was catalyzed by copper salts including CuCl [22] and CuI [23], with the This reaction was catalyzed by copper salts including CuCl [22] and CuI [23], with the of ionic liquids (ILs) [20] to obtain 4-methylene-2-oxazolidinones or 2(3H)-oxazolones. Alternatively, assistance of ionic liquids (ILs) [20] to obtain 4-methylene-2-oxazolidinones or 2(3H)-oxazolones. assistance of ionic liquids (ILs) [20] to obtain 4-methylene-2-oxazolidinones or 2(3H)-oxazolones. metal-freecatalysts,i.e.,bicyclicguanidines[24]and[DMIm]BF [25]areeffectiveinthecycloaddition Alternatively, metal-free catalysts, i.e., bicyclic guanidines [24]4and [DMIm]BF4 [25] are effective in Alternatively, metal-free catalysts, i.e., bicyclic guanidines [24] and [DMIm]BF4 [25] are effective in reatchteiocnyscloafdCdOitiownirtehacptironpsaorgfyClOic2awlciothoplrsopanardgyplricimalacroyhoalmsianedspurnimdearyrealmatinveslyunmdieldrrceolantdivietiloyns, 2 the cycloaddition reactions of CO2 with propargylic alcohols and primary amines under relatively altmhoiludgchotnhdeitpiornods,uaclthyoiuelgdhstahrepnrotdhuicgthyeienldousgahre.nMootrheiogvheern,soiulvgehr.sMalotrseaorveers,usiitlavbelrescaaltsalayrsetsusihtaobwleing mild conditions, although the product yields are not high enough. Moreover, silver salts are suitable higchateaflfiysctisenshcyowinintghehitghhreef-fcicoimenpcyoninentht eretahcrteieo-nco(mScphoenmenet3r)e[a2c6ti]o. n (Scheme 3) [26]. catalysts showing high efficiency in the three-component reaction (Scheme 3) [26]. 1 R1 solvent-free R R OH OH 50 C,0.5MPa,12h + +Ag 1 O AgR1 O R O-H C O AgWO (1 mol%) AgWO4(1mol%) 83-95% 4 3 O NR3 R=H Ph P (2 mol%) Ph3P (2 mol%) O NR 2 R2 = Alkyl, Ph R =Alkyl,Ph (eq. a) 3 1 R1 (eq. a) solvent-free R 2 R2 3 R3 = Alkyl R =Alkyl O-H CO R2 OO2- R2 O WO OW O 2- OO O O 83-95% 1 R1 =H R Ag(I)-decorated sulfonate-MOF 99% 50 C,0.5MPa,12h 2 R2 Ag(I)-decorated sulfonate-MOF O O (10 mol%), Ph P (10 mol%) 99% (10 mol%), Ph3P (10 mol%) + O NR 3 + 3 ONR3 1 (eq.b) 3 50 C,0.1MPa,DMSO,12h R3NH R=H RNH2 50 C,0.1MPa,DMSO,12h 2 2 23 R2,R3=Alkyl R , R = Alkyl R1 = H (eq. b) R2 +R + OO CO OO 33 CO2 2 2,2',2''-terpyridine (5 mol%) 2,2',2''-terpyridine (5 mol%) NR3 O NR + O NR (eq.c) 140 C,3MPa,15h 140 C,3MPa,15h R1 + (eq.c) 1 O NR3 O Scheme 3. Catalytic systems for the reactions of CO2, propargylic alcohols and primary amines. ScShcehmeme 3e.3C. Catatlaylytitcicsysysstetemssfforrtthereactions of CO2,,pprrooppaargrgyylilcicalaclochoohloslasnadndprpimriamryaraymaimneisn.es. 2 R22 R2 R2 Me R RMe 71-92% 70-89% 71-92% 70-89% 123 R1 =Me,R2 =Me,Ar,R3 =Alkyl,Ar R =Me,R =Me,Ar,R =Alkyl,ArPDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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