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Conversion of Alcohols to Alkyl Halides02:48

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This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
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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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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Selective Conversion of 5-Hydroxymethylfuraldehyde Using Cp*Ir Catalysts in Aqueous Formate Buffer Solution.

Wei-Peng Wu1, Yong-Jian Xu1, Rui Zhu1

  • 1iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. China.

Chemsuschem
|April 15, 2016
PubMed
Summary

Highly selective hydrogenation and ring-opening of 5-hydroxymethylfuraldehyde (5-HMF) to 1-hydroxy-2,5-hexanedione (HHD) was achieved using Cp*Ir(III) catalysts. Optimal pH control yielded 99% HHD selectivity, demonstrating efficient biomass conversion.

Keywords:
5-hmfbiomasshomogeneous catalysisiridiumring-opening

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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Biomass Conversion

Background:

  • 5-hydroxymethylfuraldehyde (5-HMF) is a key platform chemical derived from biomass.
  • Efficient conversion of 5-HMF to valuable products is crucial for sustainable chemistry.
  • Homogeneous catalysis offers tunable selectivity for complex organic transformations.

Purpose of the Study:

  • To develop a highly selective catalytic system for the hydrogenation and hydrolytic ring-opening of 5-HMF.
  • To investigate the influence of reaction conditions, particularly pH, on product distribution and selectivity.
  • To elucidate the reaction mechanism and assess the scalability of the process.

Main Methods:

  • Utilized homogeneous Cp*Ir(III) half-sandwich complexes as catalysts.
  • Performed hydrogenation/hydrolytic ring-opening reactions of 5-HMF.
  • Systematically adjusted reaction pH to optimize selectivity.
  • Conducted mechanistic studies and large-scale experiments (10 g-scale).

Main Results:

  • Achieved full conversion of 5-HMF to 1-hydroxy-2,5-hexanedione (HHD) with 99% selectivity at pH 2.5.
  • Identified the hydrolysis/ring-opening of 2,5-bis-(hydroxymethyl)furan as a key intermediate step.
  • Obtained an isolated yield of 85% for HHD in a 10 g-scale experiment.
  • Demonstrated high HHD yield (98% GC yield) from fructose, showcasing catalyst tolerance to acidic conditions.

Conclusions:

  • Cp*Ir(III) complexes effectively catalyze the selective conversion of 5-HMF to HHD.
  • pH control is critical for achieving high selectivity in this transformation.
  • The developed catalytic system is robust, scalable, and tolerant to acidic conditions, enabling efficient biomass valorization.