Metal cocatalyst mediated photocatalytic dehydrogenative-condensation and direct condensation cross-coupling of aniline and alcohol

Lv, Dongdong ¹Li, Yaru ²Qiao, Wei ³Zhang, Dongdong ³Mai, Yuanqiang ³Cai, Nengjun ³Xiang, Hongwei ²Li, Yongwang ²Niemantsverdriet, Hans ⁴Hao, Weichang ¹Su, Ren⁴

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作者信息

1. Beihang Univ
2. Chinese Acad Sci
3. Soochow Univ
4. Synfuels China Technol Co Ltd
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Abstract

Cross coupling of aniline and alcohol for the synthesis of imine and secondary amines represents a highly atom efficient processes, yet achieving high selectivity requires specialized catalysts and harsh reaction conditions to avoid over-hydrogenation of as-produced imines and dehydrogenation of secondary amines. Here we employ metal cocatalysts to mediate photocatalytic activation of alcohols, thus separating the stepwise dehydrogenative-condensation process to imine and the direct condensation process to secondary amine. The Rh/TiO2 promotes the photocatalytic dehydrogenation of alcohol into aldehyde and molecular hydrogen, resulting in rapid condensation of aldehyde with aniline to yield imine. In contrast, Fe/TiO2 activates the alcohol mildly without forming aldehyde and hydrogen atoms under irradiation, allowing a direct dehydrative coupling of the activated alcohol with aniline to produce secondary amine. Both Rh/TiO2 and Fe/TiO2 photocatalysts show high performance in terms of conversion, selectivity, stability and a wide substrate scope, rendering the strategy promising for applications.

Key words

Photocatalysis/Cross-coupling/Metal cocatalyst/Imines and secondary amines/Selectivity control/N-ALKYLATION/PD NANOPARTICLES/AMINE SYNTHESIS/AMINATION/CATALYSTS/IMINES/AU/MONOALKYLATION/ACTIVATION/ADSORPTION

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出版年

2022

Applied Catalysis

ISSN：0926-3373

被引量12

参考文献量52

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