Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni‐Core–Shell Catalyst

Abstract

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel‐graphitic shell‐based core–shell‐structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium‐labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni‐based hydrogenation protocol is demonstrated by gram‐scale reactions as well as efficient catalyst recycling experiments.

Hierarchical Hollow Carbon Particles with Encapsulation of Carbon Nanotubes for High Performance Supercapacitors

“…Reduced Ni 2+ species exhibit enhanced electron transfer between the surrounding support and Ni species to give a lower Ni 2ps binding energy compared to their unreduced counterparts, [ 42 ] and the presence of unreduced‐Ni 2+ at low binding energy is attributed to air exposure and oxidation prior to testing, aligning with previous findings. [ 23a,43 ]…”

Methanol as a Potential Hydrogen Source for Reduction Reactions Enabled by a Commercial Pt/C Catalyst

“…1,2-Diphenylethane (46). 70 It is obtained as a colorless solid (19.42 mg, 21%) after purification by column chromatography (n-hexane/ EtOAc: 90:10). 1 H NMR (500 MHz, CDCl 3 ): δ 7.34 (m, 4H), 7.26 (m, 6H), 2.98 (s, 4H).…”

“…13 (40). 70 It is obtained as a colorless liquid (45.21 mg, 95%) after purification by column chromatography (n-hexane/EtOAc: 90:10). 1 H NMR (500 MHz, CDCl 3 ): δ 6.76 (m, 1H), 6.67−6.57 (m, 2H), 5.45 (s, 1H), 3.88−3.76 (s, 3H), 2.51−2.41 (t, 2H), 1.64−1.47 (m, 2H), 0.96−0.81 (t, 3H).…”

“…3-Phenylpropan-1-ol (45). 70 It is obtained as a colorless liquid (14.99 mg, 22%) after purification by column chromatography (nhexane/EtOAc: 90:10). 1 H NMR (500 MHz, CDCl 3 ): δ 7.35 (t, J = 7.5 Hz, 2H), 7.29−7.22 (m, 3H), 3.70 (t, J = 6.5 Hz, 2H), 2.80−2.70 (m, 2H), 2.52 (s, 1H), 2.00−1.88 (m, 2H).…”

Non-noble Nickel-Modified Covalent Organic Framework for Partial Hydrogenation of Aromatic Terminal Alkynes

“…Transition metal-catalyzed selective hydrogenation of aromatic terminal alkynes has been reported as a straightforward and effective route for aromatic alkene synthesis. − Various noble metal (Pd, Rh, Ir, Ru, etc. )-catalyzed systems, especially the Lindlar catalyst (Pd/CaCO 3 modified by Pb­(OAc) 2 or Pd/BaSO 4 with excessive addition of quinoline), have been developed and exhibited excellent activity under mild reaction conditions in the semi-hydrogenation. − However, the presence of toxic additives leads to virulent wastes and the expensive metal improves production cost. , In recent years, the development of environmentally friendly, earth-abundant, and nonprecious metal catalysts such as iron, cobalt, copper, and nickel nanoparticles with high activity and selectivity have attracted considerable interest and seem to be promising for this hydrogenation reaction. − Pérez-Ramírez and co-workers reported heterogeneous Cu–Ni–Fe catalysts with appropriate metal ratios and the ternary Cu–Ni–Fe catalysts system displayed outstanding alkene selectivity with 100% propene selectivity and 80% ethene selectivity in the gas-phase hydrogenation of propyne and ethyne at 250 °C. Recently, they synthesized atomically dispersed iron-supported graphitic carbon nitride heterogeneous catalysts in the continuous liquid-phase semihydrogenation of various alkynes, which exhibits higher activity than larger clusters .…”