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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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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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 stereochemistry.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
7.8K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

6.4K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Screening Borane Species for Dinitrogen Activation.

Alvi Muhammad Rouf1, Chenshu Dai1, Shicheng Dong1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials, Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China.

Inorganic Chemistry
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Summary

Tired of harsh conditions for nitrogen (N2) activation? Tricoordinated boranes, acting as intramolecular frustrated Lewis pairs (FLPs), offer a promising, milder alternative for N2 fixation and reduction.

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Area of Science:

  • Computational Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Activating the strong triple bond in molecular nitrogen (N2) under mild conditions remains a significant challenge in chemistry.
  • Previous N2 fixation and reduction methods often required harsh conditions using metallic species.
  • Developing less reactive, easily prepared species for N2 activation is crucial for advancing chemical synthesis.

Purpose of the Study:

  • To investigate the potential of tricoordinated boranes for N2 activation and functionalization under mild conditions.
  • To identify optimal borane structures that can function as intramolecular frustrated Lewis pairs (FLPs) for N2 activation.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to screen and evaluate various tricoordinated borane structures.
  • Thermodynamic and kinetic factors governing N2 activation by borane-based FLPs were computationally assessed.

Main Results:

  • DFT calculations reveal that tricoordinated boranes, particularly those designed as intramolecular FLPs, can effectively activate N2.
  • Screened borane-FLP composites demonstrate favorable thermodynamic stability and low kinetic barriers for N2 binding.
  • The identified boranes show significant potential for N2 activation/functionalization under ambient conditions.

Conclusions:

  • Tricoordinated boranes represent a viable and promising class of compounds for next-generation N2 activation.
  • Borane-based FLP chemistry offers a milder alternative to traditional metallic catalysts for N2 fixation and reduction.
  • The findings encourage further experimental development of these borane systems for practical applications in nitrogen chemistry.