Extracting Mechanistic Information from an Open Data Set for a Pharma-Relevant Suzuki–Miyaura Cross-Coupling Reaction
Barnabas A. Franklin, Niall W. B. Donaldson, James D. Firth, Christopher S. Horbaczewskyj, Aaron Aspell, Theo Tanner, Adrian C. Whitwood, Julie Wilson, Jessica K. Hargreaves, Ian J. S. Fairlamb
TL;DR
This paper analyzes open data from a common pharmaceutical reaction to uncover trends in product yields and side reactions.
Contribution
The study introduces a detailed analysis of an open SMCC reaction dataset to identify trends in side-product formation and product yield.
Findings
Key trends were identified linking reaction conditions to protodeborylation side-product formation.
A Shiny app was developed to facilitate rapid evaluation of the SMCC reaction dataset.
Analysis revealed insights into how substrates, solvents, bases, and ligands affect product yields.
Abstract
Open reaction data sets, particularly those gathered through high-throughput experimental (HTE) reaction screening campaigns, hold considerable value in downstream data analysis and reaction understanding. Data can be used to reveal important trends. Such open reaction data are increasingly being reported and deposited to appropriate databases, particularly for the most popular chemical reactions, e.g., Suzuki–Miyaura cross-coupling (SMCC) of organohalides and organoboron compounds, catalyzed by Pd and mediated by a suitable base. While there is considerable complexity associated with SMCC reactions, as informed by many independent mechanistic studies over the years, one can bring out essential trends through detailed data analysis. In this study, we have taken an open reaction data set reported by Pfizer and evaluated the properties of closely related substrates and the effect of the…
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Taxonomy
TopicsCatalytic Cross-Coupling Reactions · Organoboron and organosilicon chemistry · Catalytic C–H Functionalization Methods