Related Experiment Video
Updated: Jun 28, 2026
06:26
Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
Nickel-catalyzed reductive carboxylation of styrenes using CO2
Catherine M Williams1, Jeffrey B Johnson, Tomislav Rovis
1Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Journal of the American Chemical Society
|October 22, 2008
Summary
A new nickel catalyst efficiently converts styrenes and carbon dioxide (CO2) into valuable products under mild conditions. This robust catalytic system demonstrates effective CO2 fixation even with limited reactant availability.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Sustainable Chemistry
Background:
- Carbon dioxide (CO2) utilization is a key challenge in sustainable chemistry.
- Developing efficient catalytic methods for CO2 fixation is crucial for mitigating environmental impact.
- Styrenes are versatile building blocks in organic synthesis.
Purpose of the Study:
- To develop a novel nickel-catalyzed reductive carboxylation of styrenes using CO2.
- To investigate the reaction mechanism and identify key catalytic intermediates.
- To assess the robustness and efficiency of the developed catalytic system.
Main Methods:
- Nickel-catalyzed reductive carboxylation reaction.
- Use of diethylzinc as a reductant.
- Mechanistic studies involving preliminary data analysis.
Main Results:
- Successful development of a nickel-catalyzed reductive carboxylation of styrenes with CO2.
- Reaction proceeds under mild conditions with diethylzinc as the reductant.
- Robust catalyst system achieves good CO2 fixation yields, even with equimolar CO2.
- Preliminary mechanistic insights suggest a two-step nickel-mediated catalytic cycle involving hydrozincation and carboxylation.
Conclusions:
- The developed nickel catalyst offers an efficient route for styrene carboxylation using CO2.
- The catalytic system is robust and effective even under challenging conditions (equimolar CO2).
- This work contributes to the advancement of CO2 utilization strategies in catalysis.
Related Concept Videos
01:24Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
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.
01:13Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
01:28Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
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...
02:23Alcohols from Carbonyl Compounds: Reduction
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.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...