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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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...
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Introduction
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.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.9K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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...
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Atomically precise copper clusters with dual sites for highly chemoselective and efficient hydroboration.

Teng Jia1, Jie Ai1, Xiaoguang Li2

  • 1Henan Key Laboratory of Crystalline Molecular Functional Materials and College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China.

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Copper cluster catalysts enable efficient alkyne hydroboration. A novel Cu4NC catalyst demonstrates exceptional performance, high selectivity, and reusability under mild conditions, advancing catalytic chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Alkyne hydroboration to vinylboronate esters is crucial but challenging regarding selectivity and catalyst efficiency.
  • Developing catalysts with high turnover numbers and chemoselectivity remains a significant hurdle in organic synthesis.

Purpose of the Study:

  • To develop novel copper cluster catalysts for enhanced alkyne hydroboration.
  • To investigate the catalytic performance, selectivity, and reusability of these new catalysts.
  • To elucidate the mechanistic basis for the observed catalytic activity.

Main Methods:

  • Synthesis and characterization of dual-catalytic-site copper clusters (Cu4NC and Cu8NC) with N-heterocyclic thione ligands.
  • Evaluation of catalyst performance in alkyne hydroboration under mild conditions.
  • Mechanistic studies including density functional theory (DFT) calculations.

Main Results:

  • The microcrystalline Cu4NC catalyst exhibited a high turnover number (77,786) and excellent chemoselectivity.
  • Cu4NC demonstrated high recovery and reusability, along with superior catalytic activity compared to Cu8NC.
  • DFT calculations indicated a lower activation energy for hydroboration with the Cu4NC catalyst.

Conclusions:

  • Precisely engineered cluster catalysts with dual catalytic sites can significantly enhance catalytic properties.
  • Synergistic interactions and dynamic ligand effects in Cu4NC contribute to its high catalytic activity.
  • This research provides a pathway for developing advanced cluster catalysts for improved chemical transformations.