B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> Co-Catalyst Promotes Unconventional Halide Abstraction from Grubbs I to Enhance Reactivity and Limit Decomposition

Ruthenium based Grubbs metathesis has become a commonplace reaction for synthetic chemists. Development of new generations of catalysts evolving from Grubbs I (GI) have led to greater stability, functional group compatibility, and superior reactivities. However, these advancements lead to increased costs. To this end, we report here how the addition of the commercially available tris(pentafluorophenyl)borane Lewis acid, which has become a common place catalyst in its own right, leads to enhanced reactivity of GI. Moreover, the increased reactivity arises via halide abstraction rather than traditional phosphine dissociation, providing ring-opening metathesis polymerization products that are divergent from those synthesized without the Lewis acid cocatalyst.

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Publication Details

Journal
Organometallics
Published
2024-10-23
DOI
https://doi.org/10.1021/acs.organomet.4c00178
Citations
3
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
0.75

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article

B(C6F5)3 Co-Catalyst Promotes Unconventional Halide Abstraction from Grubbs I to Enhance Reactivity and Limit Decomposition

Trandon A. Bender, Dikin Patel, Austin W. Medley, Calvin Utne
3 citations
Organometallics
Synthetic Organic Chemistry Methods
0.75
article

B(C6F5)3 Co-Catalyst Promotes Unconventional Halide Abstraction from Grubbs I to Enhance Reactivity and Limit Decomposition

Trandon A. Bender, Dikin Patel, Austin W. Medley, Calvin Utne
article en
3 citations

Abstract

Ruthenium based Grubbs metathesis has become a commonplace reaction for synthetic chemists. Development of new generations of catalysts evolving from Grubbs I (GI) have led to greater stability, functional group compatibility, and superior reactivities. However, these advancements lead to increased costs. To this end, we report here how the addition of the commercially available tris(pentafluorophenyl)borane Lewis acid, which has become a common place catalyst in its own right, leads to enhanced reactivity of GI. Moreover, the increased reactivity arises via halide abstraction rather than traditional phosphine dissociation, providing ring-opening metathesis polymerization products that are divergent from those synthesized without the Lewis acid cocatalyst.

OrganometallicsVol. 43(21)
Old Dominion University (US)
Old Dominion University, Division of Chemistry
Openalex Percentile: Top 32%
Synthetic Organic Chemistry Methods
0.75
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