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Molecules 2019, 24, 182 28 of 41 Molecules 2019, 24, x FOR PEER REVIEW 28 of 42 a) Formation of methylamine via non-formamide intermediate process CH3 N CH3 Ph N N Ph CH CH CHO N CH + CO2 + PhSiH3 K2WO4 (7.5 mol%) o CH3CN,70 C,12h K2WO4 (7.5 mol%) CH3CN, 70 oC, 12 h (eq. 1) (eq. 2) Ref. 129 Ref. 128 3 CHO 3 equiv. quantitative yield CH3 N CH 3 no reaction 3 3 + CO2 + PhSiH3 2 Ref. 120 Ref. 123 HN C H 3 Ref. 124 + CO + PhSiH CH3CN,rt.,12h N CH3 + CO2 + PMHS CH3CN,100oC,48h 0.1 MPa (eq. 3) no product DBU (1 mol%) CH3 N CH3 b) Formation of methylamine via formamide intermediate process CHO N + CH3 CHO PhSiH 3 Fe(acac)2 (5 mol%) PP3 (5 mol%) THF, 100 oC, 22 h TBAF(5mol%) CH3CN, 50 oC C H O CH3 N CH3 > 95% CH3 NCH3 95% (eq. 4) (eq.5) N + PhSiH CH3 3 1.3 equiv Cs2CO3 (5 mol%) N CH 3 1 equiv. PhSiH3 o 80 C,24h C H 3 N CH3 (eq. 6) (eq. 7) (eq. 8) Ref. 130 23 90% 32% 1 equiv. no reaction CHO N CH3 99% no reaction CH3 + Cu2(OH)2CO3 CHO Cu (OH) CO CH3 PhCyP N 223 N 2 PhSiH3, CH3CN, 60 oC, 12 h + HCOOH DPPB CH3 CH3 N CH3 87% Cu2(OH)2CO3 Ph2CyP + CO HN + PhSiH3 CH3CN, 60 oC, 12 h + HCOOH Cu2(OH)2CO3 DPPB + CO CH3 87% no reaction Scheme 32. Summarized control experiments in the published work. Scheme 32. Summarized control experiments in the published work. Increasing the reaction temperature enables a competitive and higher-energy pathway to aminal and N-methylamine, which requires direct reduction of CO2 with PhSiH3 to formoxysilane PhSiH2OOCH intermediate. The theory provided a new evidence for the pathway to formamide from aminal (Scheme 33, pathway 9).PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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