Related Experiment Video
Updated: Dec 25, 2025
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
High-Loading Single-Atom Copper Catalyst Supported on Coordinatively Unsaturated Al2 O3 for Selective Synthesis of
Tenglong Guo1, Nanfang Tang1, Feng Lin1,2
1CAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P.R. China.
Abstract:
Single-atom catalysts (SACs) as a bridge between hetero- and homogeneous catalysis have attracted much attention. However, it is still challenging to generate stable single atoms with high metal loadings, and the application of SACs in traditionally homogeneous catalytic reactions is highly desirable. Herein, a Cu SAC with a high Cu loading of 8.7 wt % supported on coordinatively unsaturated Al2 O3 was prepared and used in the amine-free synthesis of homoallylboranes. Up to 99 % conversion, 95 % 1,4-selective boration of the enals, and 48-68 % isolated yields of homoallylboranes were achieved, equaling the results of reported homogenous catalysts, and the system was more efficient and stable than nano Cu/γ-Al2 O3 . Mechanistic investigation indicated that Cu-Bpin species are the active intermediates of selective boration. The superior catalytic and recycling performance of Cu SAC paves an efficient and green path toward selective synthesis of homoallyborane fine chemicals.
More Related Videos
Related Concept Videos
02:47Alkynes 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.
03:08Hydroboration-Oxidation of Alkenes
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
02:15Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
02:17Reduction 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...