Related Experiment Video
Updated: Jun 7, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
B(C6F5)3 Co-Catalyst Promotes Unconventional Halide Abstraction from Grubbs I to Enhance Reactivity and Limit
Austin W Medley1, Diya Patel1, Calvin Utne1
1Department of Chemistry and Biochemistry, Old Dominion University, 4501 Elkhorn Avenue, Norfolk, Virginia 23529, United States.
Adding tris(pentafluorophenyl)borane Lewis acid enhances Grubbs I catalyst reactivity for ring-opening metathesis polymerization. This cost-effective method achieves divergent products via halide abstraction, not phosphine dissociation.
Area of Science:
- Organic Chemistry
- Polymer Chemistry
- Catalysis
Background:
- Ruthenium-based Grubbs catalysts are widely used in organic synthesis.
- Newer generations offer improved stability and reactivity but are costly.
- Cost-effective alternatives for enhancing catalyst performance are needed.
Purpose of the Study:
- To investigate the effect of tris(pentafluorophenyl)borane on Grubbs I catalyst reactivity.
- To explore a cost-effective method for improving ruthenium-based metathesis reactions.
- To understand the mechanism of reactivity enhancement.
Main Methods:
- Utilized Grubbs I catalyst in ring-opening metathesis polymerization.
- Introduced tris(pentafluorophenyl)borane as a Lewis acid co-catalyst.
- Analyzed reaction products and compared them to those synthesized without the co-catalyst.
Main Results:
- Tris(pentafluorophenyl)borane significantly enhanced the reactivity of Grubbs I.
- The enhanced reactivity was attributed to halide abstraction, not phosphine dissociation.
- Divergent ring-opening metathesis polymerization products were obtained.
Conclusions:
- Tris(pentafluorophenyl)borane is an effective and economical co-catalyst for Grubbs I.
- This approach offers a novel pathway to diverse polymer structures.
- The findings provide a new strategy for tuning metathesis polymerization.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Nucleophilic Aromatic Substitution: Elimination–Addition
Radical Substitution: Allylic Bromination
Base-Promoted α-Halogenation of Aldehydes and Ketones
Elimination Reactions