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Updated: Mar 27, 2026
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
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Extracting Mechanistic Information from an Open Data Set for a Pharma-Relevant Suzuki-Miyaura Cross-Coupling Reaction
Barnabas A Franklin1, Niall W B Donaldson1, James D Firth1
1Department of Chemistry, University of York, Heslington, York, North Yorkshire YO10 5DD, U.K.
Organic Process Research & Development
|March 26, 2026
Summary
Analyzing Suzuki-Miyaura cross-coupling (SMCC) reaction data reveals trends in side-product formation. Evaluating yields of main products versus protodeborylation byproducts offers valuable insights for reaction optimization.
Area of Science:
- Organic Chemistry
- Chemical Data Analysis
- Reaction Optimization
Background:
- Open reaction data, especially from high-throughput experimentation (HTE), is crucial for understanding chemical reactions.
- Suzuki-Miyaura cross-coupling (SMCC) is a widely used reaction, generating extensive data valuable for trend analysis.
- Understanding side-product formation, like protodeborylation, is key to optimizing SMCC reactions.
Purpose of the Study:
- To analyze an open reaction dataset from Pfizer focusing on Suzuki-Miyaura cross-coupling.
- To investigate the influence of substrates, solvents, bases, and ligands on SMCC outcomes.
- To identify and analyze trends related to protodeborylation, a common side-product in SMCC.
Main Methods:
- Utilized an existing open reaction dataset from a high-throughput screening campaign.
- Performed detailed data analysis to evaluate reaction yields and side-product formation.
- Developed a Shiny application for rapid data set evaluation.
Main Results:
- Identified key trends by comparing main cross-coupled product yields with protodeborylated byproduct formation.
- Evaluated the impact of closely related substrates, reaction solvents, bases, and ligands on SMCC outcomes.
- Demonstrated the value of analyzing side-product yields in conjunction with main product yields.
Conclusions:
- Detailed analysis of open reaction data, including side-product formation, provides significant insights into SMCC reactions.
- The study highlights the importance of evaluating protodeborylation in relation to desired product formation.
- A developed Shiny app facilitates efficient analysis of SMCC reaction data.
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