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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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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.
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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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.
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
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Atomically Precise Metal Nanoclusters as Single Electron Transferers for Hydroborylation.

Wanli Zhu1,2, Sheng Zhang1,2, Weigang Fan1,2

  • 1Institute of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. China.

Precision Chemistry
|August 29, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a new single electron transfer (SET) catalysis mode for metal nanoclusters, enhancing catalytic activity and stability. This approach overcomes ligand inhibition, enabling efficient alkyne hydroborylation under mild conditions.

Keywords:
atomically precise metal nanoclusterboryl radicalhydroborylationsingle electron transfertandem catalysis

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Area of Science:

  • Nanoscale Science
  • Catalysis
  • Materials Chemistry

Background:

  • Metal nanoclusters offer precise structures for studying nanoscale catalysis.
  • Ligands on nanocluster catalysts often inhibit activity by deactivating surfaces.
  • A balance between catalytic activity and stability is crucial for nanocluster catalysts.

Purpose of the Study:

  • To introduce a novel catalytic mode for metal nanoclusters.
  • To address the challenge of ligand inhibition in nanocluster catalysis.
  • To provide a solution for the trade-off between activity and stability in metal nanocluster catalysts.

Main Methods:

  • Initiation of catalysis via single electron transfer (SET) without nanocluster degradation.
  • Application of the novel mode in alkyne hydroborylation reactions.
  • Demonstration of catalyst recycling and application in tandem processes.

Main Results:

  • The novel SET activation mode enables catalysis without destroying nanocluster integrity.
  • Achieved low catalyst loading (0.01 mol%), high turnover frequency (TOF), and mild reaction conditions.
  • Successfully applied the catalyst [Au1Cu14(TBBT)12(PPh3)6]+ in alkyne hydroborylation, improving selectivity and functional group tolerance.
  • Demonstrated efficient tandem reactions, including hydroborylation-deuteration and hydroborylation-isomerization.

Conclusions:

  • The developed single electron transfer (SET) catalytic mode offers a viable solution to ligand inhibition in metal nanocluster catalysis.
  • This approach enhances both the activity and stability of nanocluster catalysts.
  • The demonstrated utility in alkyne hydroborylation and tandem reactions highlights the broad applicability of this novel catalytic strategy.