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Acid Halides to Ketones: Gilman Reagent01:14

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the...
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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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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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Heterogeneous Catalysis01:22

Heterogeneous Catalysis

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Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
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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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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Why Is Methanol Formation Suppressed in CO2 Reduction Over Copper Electrocatalysts?

Zhanzhao Fu1,2, Aoni Xu3, Chunyao Fang1

  • 1State Key Laboratory of Clean Energy Utilization, College of Energy Engineering, Zhejiang University, Hangzhou, China.

Angewandte Chemie (International Ed. in English)
|April 20, 2026
PubMed
Summary

Electrocatalytic reduction of carbon dioxide (CO2RR) to methanol is hindered by competing methane and C2+ product formation on copper catalysts. This study reveals kinetic limitations and proposes a strategy to enhance methanol selectivity.

Keywords:
CO2 reductionconstant potential simulationsexplicit solvent modelproduct selectivityreaction mechanism

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Area of Science:

  • Electrochemistry
  • Catalysis
  • Computational Chemistry

Background:

  • Electrocatalytic CO2 reduction (CO2RR) offers a sustainable route to methanol (CH3OH) synthesis, contrasting with energy-intensive industrial methods.
  • Copper (Cu) catalysts typically yield methane (CH4) and C2+ products, suppressing CH3OH formation in CO2RR.
  • Understanding the intrinsic mechanisms governing product selectivity is crucial for advancing CO2RR.

Purpose of the Study:

  • To elucidate the fundamental thermodynamic and kinetic factors responsible for the suppression of methanol formation during electrocatalytic CO2 reduction on Cu.
  • To identify key intermediates and reaction pathways that dictate product selectivity.
  • To propose a theoretical strategy for enhancing methanol selectivity in CO2RR.

Main Methods:

  • Utilized constant-potential explicit solvent computational methods to systematically investigate reaction pathways.
  • Compared thermodynamics and kinetics of C2+ products, CH4, and CH3OH formation.
  • Analyzed 21 potential C-C coupling pathways and C1 product formation mechanisms.

Main Results:

  • Identified nine C-C coupling pathways with significantly lower activation barriers than C1 products, indicating facile C2+ formation.
  • Determined that the *CH2OH intermediate favors C-O bond cleavage to CH4 over hydrogenation to CH3OH, kinetically hindering methanol production.
  • Simulated Faradaic efficiencies aligned with experimental trends, validating the proposed mechanism across different Cu surfaces and potentials.

Conclusions:

  • The intrinsic suppression of methanol in CO2RR on Cu catalysts stems from the preferential C-O cleavage of the *CH2OH intermediate.
  • A proposed strategy involves redirecting the reaction pathway via *COOH to *HCOO and stabilizing *CH2OH to promote hydrogenation to CH3OH.
  • These findings provide a mechanistic basis for designing catalysts and conditions for selective methanol synthesis via CO2 electroreduction.