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Molecules 201M9,o2le4c,uxleFsO20R1P9,E2E4R, xRFEOVRIEPWEER33REoVf I4E2W Molecules 201M9,o2le4c,uxleFsO20R1P9,E2E4R, xRFEOVRIEPWEER33REoVf I4E2W Molecules 201M9,o2le4c,uxleFsO20R19P,E2E4R, xRFEOVRIEPWEER33REoVf I4E2W Molecules 2019, 24, x FOR PEER REVIEW 33 of 42 Molecules 2019, 24, x FOR PEER REVIEW 33 of 42 33 of 42 33 of 42 33 of 42 Table 5. N-TFoabrmley5la. tNio-nForfmtyplaictiaolnamofintyepsiwcailthamCiOn2e/sHw2. ith CO2/H2. Table 5. N-Formylation of typical amines with CO2/H2. Table 5. N-Formylation of typical amines with CO2/H2. Table 5. N-TFoarbmley5la. tNio-nForfmtyplaictiaolnamofintyepsiwcailthamCiOn2e/sHw2. ith CO2/H2. Molecules 2019, 24, x FOR PEER REVIEW 33 of 42 Table 5. N-Formylation of typical amines with CO2/H2. Table 5. N-Formo ylation of otypical amines with CO2/H2. a,b a,b a PCrodn.v./% ConYvi./e%ld/% YieRledf/.% Entry SEunbt.ry Sub. Cat. Cat.PCO2 /MPa PCPOH2 2//MPa PTHe2m/MpP./aC TTem/hp./ C STo/lh. SolP. rod. a Ref. Ref. Molecules 2019, 24, 182 Entry Entry Entry 32 of 41 Sub. Cat. Sub. Cat. Pd/C Table 5. N-TFaobrmley5la. tNio-nFoorfmotyplaitciaolnaomfiotnyepsicwailthamCiOne2/sHw2.ith CO2/H2. PCO2 /MPa PH2/MPa Temp./ C T/h Sol. Prod. Conv./% a,b a,b a Yield/% Ref. Entry Sub. Cat. PCO2 /MPa PH2/MPa Temp./ C T/h Sol. Prod. Conv./% Yield/% a 1 P d / C P d / C 1 1 3 13 0 5 CatP. CO2 /TMaPbaleP5C.PONH2 2/-/MFMoPrPma ylaPTtHieo2m/nMpoPf./atCypiTcaTelm/ahmp.i/nCes wSTiot/lh. CO2/HS2. olP. rod. 1 2 14 0 5 M e 2O4 H M e O H oo NA NA93 a,b a,b a [19437] YieRledf/.% [147] SEunbt.ry 1 1 n Entry BSuuNbH. 2 Table 5.TNab-Fleo5rm. Ny-lFaotriomnyloaftitoynpoicfatylpaimcailnaemsiwneisthwCithOC2/OH22/.H2. PCrodn.v./% ConYvi.e/%ld/% a Ref. 1 1Table 5. N3-Formylat1io0n5 of typ2i4cal amMineOsHwith CO /H . Pd/C 1 3 105 24 MeO2H2 NA 93 [147] NA 93 [147] 2 o o P d / C 1 1 3 1 3 0 5 2 1 4 0 5 M e 2 O 4 H M B e Ou NH H C H O B u N H C N H A O N A 7 7 a Ref. n SEunbt.ry BuN2H2 n Sub. Cat. B u N H P 2 d / C a,b a,ba Cat.PCO2 /MPa PCPOH2 2//MPa PTHe2m/MpP./aC TTem/hp./ C STo/lh. nSolP. rod. n PCrodn.v./% ConYvi./e%ld/% YieRledf/.% [1747] 1 Pd/C Pd/C 1 21405 Me2O4H MeOH NA NA93 [19437] [147] Sub. Cat. mp./oC T/h nSol. Prod. 2/4h MSeoOl.H BuNPrHodC.HOn ConNvA./% a,bConv./% a,b Yie7ld7/% Yield/% a [147] En2try 1 2 n PCda/tC. BuNH2 PCO2 1/MPa Pd/C 105 24 MeOH BuNHCHO NA a [R14e7f.] 77 Ref. Pd/C [147] 3 1 Pd/C 1 21405 Me2O4H MeOH NA Pd−Au/PANPdI-−CANuT/PANI-C3N.5T 41825 1,4-di4o8xane1,4-dioxane >99.9 NA93 >99.98.3 [19437] [9184.83] [147] 2 3 BuNHP2d/C Pd/C 1 13 1305 o 21405 Me2O4H MBeuONHHCHOBuNHCNHAO a,b NA77 a [1747] [148] Entry BuN2H2 n Sub. n Cat. PCO2 /MPa PH2/MPa Temp./ C T/h o Sol. n Prod. n Conv./% Yielda/,b% Ref. a [147] Entry Teomp./ C T/h Sol. Prod. Conv./% Sub. Cat. P /MPa P /MPa Temp./o C T/h Sol. Prod. Conv./%a,b Sub.1 Pd−Au/PCPdAa/tCN. I-CNTPd/C PC3O1.252 /MPa 13P3.H52/MPa 1312T05emp./ 4C218405 T1/,h4M-dei2oO4xHaneSoMl. eOH Prod. >N99A.9 ConvN./A%9983.3 a,b Yield/% aRef. [14R7e] f. Entry Sub. Cat. PCO2 /MPa PH2/MPa Entry31 2 3 Pd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane >99.9 Yield/a% Yi[1e194l3d87]/% Ref. 1 13 1305 21405 nn 98.3 [148] nBuN2H2 BuNHP2 d/C Pd/C Me2O4H MnBeOuNHHCHOBuNHCNHAO NA77 [1747] 4 nn nn [147] BuN4H2 PBdu−NAHu/2PANPdI-−CANuT/PANI-C3N.5T 3.35.5 31.525 41825 1,4-di4o8xane1,4-dBiuoxNaHneCHOBuNHC6H3.O1 63.162.2 [6124.82] [148] 3 3 P d − A u / P A N P d I - − C A N u T / P A N I - C 3 N. 5 T 3 . 3 5 . 5 31.525 41825 1,4-di4o8xane1,4-dioxane >99.9 >99.98.3 [9184.83] [147] 93 [148] 1 1 PPdd/C/C 1 1 3 3 105 105 24 M24eOH MeOH NA N9A3 [147] [ 1 [4 18 4] 7 ] 1 4 BuNHP2 d/CPd−Au/PANI-CNT1 3 125 2 nn nn nBuN2H2 BuNH2 nBuNHP2 d/C Pd/C 1 Pd−Au/PANI-CNT 3.5 13 3.5 3105 2 1 4 0 5 M e 2 O 4 H M n B e Ou NH H C H On B u N H C N H A O NA 77 48 1,4-dioxane BuNHCHO 63.1 62.2 [17477] [148] 629.23 [147] 1 Pd/C 1 3 105 24 MeOH NA 125 24 48 M1e,O4-Hdioxane nBuNHCHO N63A.1 93 [147] 3 n4 Pd−Au/PANPdI-−CANuT/PANI-C3N.5T Pd/C 1 3.5 3.5 105 41825 1,4-di4o8xane1,4-dioxane >99.9 >99.98.3 24 MeOH BuNHCHO NA 2 3 3 3.35.5 3.35.5 31.525 31.525 [9184.83] [134.48] 77 [148] 5 BuNH2 Pn d−Au/PANPdI-−CANuT/PANI-C3N.5T n P B d u − NA Hu / P 2 P d A / C NP d I - − C A N u T / P A N I - C 3 1 N. 5 T 3 3.35.5 3.5 105 31.525 125 41825 1,4-di4o8xane1,4-ndioxane n 4.1 4.1 3.4 4218425 1,4M-dei4Oo8xHane1,4-dBiuoxNaHneCHOn BuNHC6NH3A.1O 63.16727.2 [147] [148] 42 n 5 BuN4H2 3.353.5 1 31.5205 3 [6124.872] 77 [148] 2 BuNH2 Pd/C 105 24 MeOH BuNHCHO NA [147] 3 3 PdP−dA−uA/uP/APNPAdIN-−CAI-NCuT/NPTANI-C3N.35.T5 Pn d−AuP/PdA/CNPdI-−CANuT/PANI-C3N.5T1 41825 1,44-d8i4o8xane1,4-dioxane >99.9 >9>9.98..93 41825 21,4-di4o8xaMne1e,O4-HndioxanenBunNHCH4O.1 N 4 A. 1 3 . 4 [9184.83]98.3 [1347.487] [148] [148] [ 1 [4 18 4] 7 ] 2 5 3.35.5 3 3.5 31.525 105 4 n BuNH PBdu−NAHu/2PANPdI-−CANuT/PANI-C3N.5T 3.35.5 3.5 31.525 125 41825 1,4-di4o8xane1,4-dBiuoxNaHneCHOBuNHC6H3.O1 63.162.2 48 1,4-dioxane n BuNHCHO 63.1 [6124.82] [148] nBnuNH52 BuN4H2 6 PPd−Au/PANPNdII-−-CANuT/TPANI-C3N.53T.5 3.35.5 3.5 31.525 5 PdP−dA−uA/PuA/PNPAdIN-−CAIN-CuT/NPTANI-C3N.35.T5 3.35.5 3.5 31.525 4 3 Pd−Au/PANI-CNT 3.5 Pd−Au/PANI-CNT 3.5 Pd−Au/PANPdI-−CANuT/PANI-C3N.5T 125 48 1,4-dioxane >99.9 98.3 62.2 [148] [148] 5 4.1 >949.1.93.4 [91384..483] [6124.82] [148] [ 1 [4 18 4] 8 ] 2 [148] 35 BuN4H2 PBdu−NAHu/2PANPdI-−CANuT/PANI-C3N.5T 3.35.5 31.525 3.35.5 31.525 nn nn 41825 1,4-di4o8xane1,4-dioxane 41825 1,4-di4o8xane1,4-dBiouxNaHneCHOBuNHC6H3.O1 63.162.2 3 4 125 41825 41,84-di4o81x,a4n-ed1i,o4-xdainoxeane 0.2 >909..290.1 41825 1,4-4d8i4o8xane1,,4-diioxane 4.1 4.143.1.4 [1094.818.]3 [134.48]3.4 5 6 125 [148] [148] [148] 5 4 nBuNH2 nPd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane nBuNHCHOn 63.1 62.2 125 48 1,4-dioxane BuNHCHO 63.1 [148] 6 4 BuNH2 Pd−Au/PANI-CNT 3.5 3.5 62.2 Pd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane 0.2 0.1 [148] 6 Pd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane 0.2 0.1 [148] 4 5 5 Pd−Au/PANPdI-−CANuT/PANI-C3N.5T 3.35.5 31.525 nBuNH2 Pd−Au/PANI-CNT 3.5 3.5 125 41825 1,4-di4o8xane1,4-dioxane 4.1 4.1 3.4 48 1,4-dioxane nBuNHCHO 63.1 [134.48] 62.2 [148] 6 6 5 7 6 57 8 6 7 8 6 PdP−dA−uA/PuA/PNPAdIN-−CAIN-CuT/NPTANI-C3N.35.T5 3.35.5 3.5 31.525 41825 1,4-4d8i4o8xane1,,4-diioxane 0.2 0.200.2.1 [104.18] 0.1 [148] [148] Pd−Au/PANI-CNT 3.5 3.5 125 125 48 1,4-dioxane 4.1 3.4 [148] [148] [148] 5 Pd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane 4.1 3.4 7 P d / N C P d / N C 3 3 4 14 3 0 6 Pd−Au/PANPdI-−CANuT/PANI-C3N.5T 3.35.5 31.525 21430 etha2n4ol ethanol NA NA94 41825 1,4-di4o8xane1,4-dioxane 0.2 0.2 0.1 [19448] [104.18] [148] [148] 7 Pd−AuP/PdPd/AN/NCCI-CNT 33.5 7 Pd/NC 3 4 34.5 130 4 112350 130 24 48e2th4an1o,4l -dioetxhaaneol NA 4.1N9A4 [1348.4] 94 94 [148[]148] [148] 6 Pd−Au/PANPdI-−CANuT/PANI-C3N.5T 3.35.5 31.525 7 7 Pd/NC Pd/NC 3 34 1430 130 24 ethanol NA 6 [148] 41825 1,4-di4o8xane1,4-dioxane 0.2 0.2 0.1 [104.18] NA NA94 [19448] [148] 6 6 Pd−Au/PANI-CNT 3.5 3.5 125 21430 etha2n4ol ethanol 48 1,4-dioxane 0.2 0.1 [148] 8 8 PPdd/N/NCC Pd/NC 3 3 34 4 1430 P d / N C P d / N C 3 3 4 14 3 0 21430 e2th4a2n4ol ethanol NA 21430 etha2n4ol ethanol NA NAN1A1 NA94 [11418] 11 [19448] [148] [148] [148] Pd−Au/PANI-CNT 3.5 3.5 125 48 1,4-dioxane 0.2 0.1 [148] 13 1305 PCPO2H2//MPaa PTHe2/mMpP./aC TeT 3 105 o 13 1 3 13 0 5 3.35.5 31.525 7 7 8 Pd/NC 3 4 130 24 ethanol NA 11 [148] 8 Pd/NC 3 4 130 24 ethanol NA 11 [148] 7 P d / N C P d / N C 3 3 4 21430 eth2a4nol ethanol NA 48 1,4-dioxane 7 41 3 0 aaa bbb NA 94 0.2 [1948] 0.1 [148] Pd−Au/PANI-CNT 3.5 3.5 125 [148] 8 7 8 8 8 8 Pd/NC Pd/NC 3GGCCcocnovnevrseir3Gos4niCoancnodannyvdieerlysdioeb14nlad3sa0ebndasoyenidealodm2nbi14na3esm0.edinNoeone.ttahamvNa2ain4noioletal.balveNa(oieNltatAhabval)ae.niol(aNlbAle)(.NA). NA NA11 94 [11418] [148] [148] Pd/NC Pd/NC Pd/NC Pd/NC Pd/NC Pd/NC a Pd/NC Pd/NC 3 4 130 24 ethanol NA 7 3 4 130b 24 ethanol NA 94 [148] 8 3GC conversi3o4n and yield b14a3s0ed on am2i14n3e0. Noetthava2an4iolalble (eNtAha).nol NA a GC conversion and yield based on amine. b Not available (NA). NA11 [11418] [148] aa bb GC conversiGonCacnodnyvierlsdiobnasaendoyniealmd binaes.edNoontamvainilea.bleN(oNt Aav)a. ilable (NA). P d / N C P d / N C 3 3 4 41 3 0 2 14 3 0 e t h 2a 4n o l e t h a n o l 8 8 3 4 130 24 ethanol NA NA 11 NA 11 [1418] 94 [148] aa bb GC conversiGonCacnodnyvieerlsdiobnasaendoyniealdmbinaes.edNoontaamvainilea.bleN(oNt Aav)a.ilable (NA). 3 4 130 24 ethanol NA [148] 3 4 130 24 ethanol aa bb GC conversiGonCacnodnvyeierlsdiobnaasend oyniealdmbinaes.edNonotaamvianilea.blNe (oNt aAv)a.ilable (NA). NA NA [148] [148] [148] 11 a GC conversaion and yield based on amine. b Not availabble (NA). GC conversion and yield based on amine. Not available (NA). 3 4 130 24 ethanol 11 a GC conversion and yield based on amine. b Not available (NA).PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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