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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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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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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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Acid Halides to Alcohols: LiAlH4 Reduction01:19

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
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Introduction
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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
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Interfacial π-π Stacking Interaction Promotes H2-Driven Enzymatic Asymmetric Reduction.

Wei Lan1, Jingru Yang1, Jiabao Wei1

  • 1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory of Advanced Catalysis and Adsorption Materials, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, 321004, China.

Angewandte Chemie (International Ed. in English)
|January 16, 2026
PubMed
Summary

This study introduces a Pickering emulsion microreactor for efficient NADH regeneration using H2. The system achieves high selectivity and over 2000 cycles, advancing sustainable chemoenzymatic reductions.

Keywords:
NAD+ hydrogenationasymmetric reductionchemoenzymatic catalysisπ–π stacking interaction

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Area of Science:

  • Biocatalysis and Green Chemistry
  • Materials Science and Engineering
  • Chemical Engineering

Background:

  • In situ hydrogen (H2)-driven nicotinamide adenine dinucleotide (phosphate) (NAD(P)H) regeneration is crucial for sustainable chemoenzymatic reductions.
  • Challenges include low selectivity in NAD(P)H formation and mutual deactivation between chemical catalysts and enzymes, hindering efficiency.

Purpose of the Study:

  • To develop a novel oil-in-water Pickering emulsion microreactor for highly selective and efficient in situ NADH regeneration.
  • To construct a chemoenzymatic microreactor for asymmetric reductive resolution using the developed NADH regeneration system.

Main Methods:

  • Utilized an oil-in-water Pickering emulsion microreactor with interfacial π-π stacking for directional H* transfer.
  • Integrated the NADH regeneration system with horse liver alcohol dehydrogenase (HLADH) for asymmetric reductive resolution.
  • Employed H2 as the reductant for the chemoenzymatic process.

Main Results:

  • Achieved >99% selectivity in NADH regeneration.
  • Demonstrated >99% enantiomeric excess (ee) for the chiral alcohol product, (S)-(-)-2-phenyl-1-propanol.
  • Sustained over 2000 NADH regeneration cycles, a record for H2-driven systems.

Conclusions:

  • The Pickering emulsion microreactor effectively separates catalysts, mitigating deactivation and enhancing NADH regeneration efficiency.
  • This approach offers a promising strategy for developing sustainable and efficient chemoenzymatic microreactors for chiral chemical production.