Non-noble Nickel-Modified Covalent Organic Framework for Partial Hydrogenation of Aromatic Terminal Alkynes
Nan Wang1,2, Jianguo Liu3, Mingyue Zhang2
1School of Environmental Science and Engineering, Tianjin University, Tianjin 300350, China.
Abstract:
Developing non-noble metal-based catalysts with excellent performance for selective hydrogenation of alkynes under mild reaction conditions is highly desirable but still faces challenges. Herein, a non-noble nickel-modified covalent organic framework (Ni/COF) had been synthesized through a facile post-modified method and followed by reduction at a different temperature under a H2/Ar atmosphere. The as-prepared catalysts were characterized by X-ray diffraction, high-resolution transmission electron microscopy, X-ray photoelectron spectroscopy, Brunauer-Emmett-Teller, and Fourier transforms infrared, and the optimal H350-Ni/COF presents excellent catalytic performance in the semihydrogenation of a series of aromatic terminal alkyne substrates, particularly in the partial hydrogenation of phenylacetylene with nearly full conversion and 85% selectivity toward styrene under mild reaction conditions (10 bar of H2, 100 °C, and 1 h). Moreover, such a catalyst also exhibited satisfying stability after three consecutive cycles.
More Related Videos
Related Concept Videos
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.


