Efficient Hydrogenation of Nitrogen Heterocycles Catalyzed by Carbon-Metal Covalent Bonds-Stabilized Palladium Nanoparticles: Synergistic Effects of Particle Size and Water

• Published in: Advanced synthesis & catalysis Vol. 358; no. 19; pp. 3039 - 3045
• Main Authors: Zhang, Yu, Zhu, Jie, Xia, Yun-Tao, Sun, Xiao-Tao, Wu, Lei
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 06.10.2016; Wiley
• Subjects: Bonding; carbon-metal covalent bonds; Catalysis; Catalysts; catalytic hydrogenation; Chemistry; Chemistry, Applied; Chemistry, Organic; Covalence; Hydrogenation; Nanoparticles; Nitrogen; nitrogen heterocycles; Palladium; Physical Sciences; Science & Technology; stabilized palladium nanoparticles; synergistic effects; MECHANISTIC ASPECTS; HIGHLY SELECTIVE HYDROGENATION; catalytic hydrogenation; RUTHENIUM NANOPARTICLES; synergistic effects; carbon-metal covalent bonds; stabilized palladium nanoparticles; PI-REARRANGEMENT; IONIC LIQUID; (ETA-5-CYCLOPENTADIENYL)RUTHENIUM CATION; MILD CONDITIONS; COUPLING REACTIONS; CHEMOSELECTIVE HYDROGENATION; nitrogen heterocycles; ASYMMETRIC HYDROGENATION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201600505

We reveal here the first hydrogenation of nitrogen heterocycles catalyzed by carbon–metal covalent bonds‐stabilized palladium nanoparticles in water under mild conditions. Using a one‐phase reduction method, smaller metal–carbon covalent bond‐stabilized Pd nanoparticles were prepared with a size distribution of 2.5±0.5 nm, which showed extraordinary synergistic effects with water in the catalytic hydrogenation of nitrogen heterocycles. Water was supposed to accelerate substrate absorption and synergistic activation of molecular hydrogen on the Pd nanoparticles surface. The nanosized Pd catalyst could be easily recovered and reused for 5 runs.