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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.
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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 Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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One-atom-thick hexagonal boron nitride co-catalyst for enhanced oxygen evolution reactions.

Yizhen Lu1, Bixuan Li2,3, Na Xu1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

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Hexagonal boron nitride (hBN) acts as a highly efficient co-catalyst for electrochemical water splitting, significantly boosting oxygen evolution reaction (OER) performance. This one-atom-thick material enhances current by ten times and shows superior mass activity compared to commercial catalysts.

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Area of Science:

  • Materials Science
  • Electrochemistry
  • Catalysis

Background:

  • Efficient co-catalysts with optimized interfacial properties are crucial for advancing electrochemical water splitting and the oxygen evolution reaction (OER).
  • Current OER catalysts face limitations in mass and charge transport, hindering overall water splitting efficiency.

Purpose of the Study:

  • To investigate the potential of one-atom-thick hexagonal boron nitride (hBN) as a co-catalyst for enhancing OER efficiency.
  • To elucidate the interfacial mechanisms responsible for improved catalytic activity in hBN-encapsulated electrodes.

Main Methods:

  • Encapsulation of various electrocatalytic electrodes with centimeter-sized, dense, and impermeable hexagonal boron nitride (hBN) films.
  • Electrochemical characterization of hBN-covered Ni-Fe (oxy)hydroxide anodes, including Tafel slope analysis and current density measurements.
  • Isotope experiments and simulations to probe reaction mechanisms and interfacial electron transfer.

Main Results:

  • hBN-covered Ni-Fe (oxy)hydroxide anodes exhibited an ultralow Tafel slope of ~30 mV dec⁻¹ and a tenfold increase in reaction current (~2000 mA cm⁻² at ~490 mV overpotential) sustained for over 150 hours.
  • The mass activity of the hBN co-catalyst surpassed that of commercial catalysts by up to five orders of magnitude.
  • Isotope experiments and simulations indicated that oxygen-containing intermediates adsorb onto the insulating hBN, facilitating deprotonation via localized electrons with minimal impedance.

Conclusions:

  • One-atom-thick hexagonal boron nitride (hBN) serves as a highly effective co-catalyst for the oxygen evolution reaction (OER) in electrochemical water splitting.
  • The enhanced performance is attributed to the unique interfacial properties of hBN, enabling efficient electron transfer and intermediate adsorption.
  • This study provides critical insights into interfacial reaction mechanisms at the atomic layer of electrodes, paving the way for next-generation electrocatalyst design.