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Molecules 2019, 24, x FOR PEER REVIEW Molecules 2019, 24, 182 Molecules 2019, 24, x FOR PEER REVIEW 23 of 42 23 of 42 23 of 41 Scheme 23. Thiazolium carbene-based catalyst for N-formylation/N-methylation. Scheme 23. Thiazolium carbene-based catalyst for N-formylation/N-methylation. Scheme 23. Thiazolium carbene-based catalyst for N-formylation/N-methylation. Subsequently, the He group [123], Fu group and Lin group [124] reported the selective Subsequently, the He group [123], Fu group and Lin group [124] reported the selective synthesis Subsequently, the He group [123], Fu group and Lin group [124] reported the selective synthesis of formamides or methylamines from amines, CO2, and hydrosilane under the different of formamides or methylamines from amines, CO2, and hydrosilane under the different catalytic synthesis of formamides or methylamines from amines, CO2, and hydrosilane under the different catalytic conditions in the same year. In He’s work, butylammonium fluoride (TBAF) was used for conditions in the same year. In He’s work, butylammonium fluoride (TBAF) was used for the reductive catalytic conditions in the same year. In He’s work, butylammonium fluoride (TBAF) was used for the reductive functionalization of CO2 with amines to selectively afford formamides or functionalization of CO2 with amines to selectively afford formamides or methylamines by employing the reductive functionalization of CO2 with amines to selectively afford formamides or methylamines by employing different hydrosilanes (Scheme 24). Formamides were obtained with different hydrosilanes (Scheme 24). Formamides were obtained with triethoxysilane as reductant, and methylamines by employing different hydrosilanes (Scheme 24). Formamides were obtained with triethoxysilane as reductant, and methylamines with phenylsilane in excellent yield und◦er methylamines with phenylsilane in excellent yield under atmospheric pressure of CO2 at 30 and 50 C, triethoxysilane as reductant, and methylamines with phenylsilane in excellent yield under atmospheric pressure of CO2 at 30 and 50 °C, respectively. The mechanism of formation of the key respectively. The mechanism of formation of the key silyl formate intermediate in the formylation step atmospheric pressure of CO2 at 30 and 50 °C, respectively. The mechanism of formation of the key silyl formate intermediate in the formylation step and fluoride-promoted hydride transfer from the and fluoride-promoted hydride transfer from the hydrosilane to CO2/formamide was proposed. silyl formate intermediate in the formylation step and fluoride-promoted hydride transfer from the hydrosilane to CO2/formamide was proposed. hydrosilane to CO2/formamide was proposed. Scheme 24. TBAF catalysis for selective N-formylation/N-methylation. Scheme 24. TBAF catalysis for selective N-formylation/N-methylation. Scheme 24. TBAF catalysis for selective N-formylation/N-methylation. The Fu group and Lin group developed a simple and effective alkali-metal carbonate, i.e., The Fu group and Lin group developed a simple and effective alkali-metal carbonate, i.e., cesium carbonate, that catalyzed both the formylation and methylation reactions under mild The Fu group and Lin group developed a simple and effective alkali-metal carbonate, i.e., cesium carbonate, that catalyzed both the formylation and methylation reactions under mild conditions (Scheme 25). Through varying the reaction temperature and loading of silane, the cesium carbonate, that catalyzed both the formylation and methylation reactions under mild conditions (Scheme 25). Through varying the reaction temperature and loading of silane, the formylation/methylation selectivity could be conveniently controlled. By means of experimental conditions (Scheme 25). Through varying the reaction temperature and loading of silane, the formylation/methylation selectivity could be conveniently controlled. By means of experimental and and computational studies, they revealed the possible mechanism including: (i) activation of Si−H by formylation/methylation selectivity could be conveniently controlled. By means of experimental and computational studies, they revealed the possible mechanism including: i) activation of Si−H by computational studies, they revealed the possible mechanism including: i) activation of Si−H byPDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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