Deciphering complexity in Pd–catalyzed cross-couplings

George E. Clarke, James D. Firth, Lyndsay A. Ledingham, Chris S. Horbaczewskyj, Richard A. Bourne, Joshua T. W. Bray, Poppy L. Martin, Jonathan B. Eastwood, Rebecca Campbell, Alex Pagett, Duncan J. MacQuarrie, John M. Slattery, Jason M. Lynam, Adrian C. Whitwood, Jessica Milani, Sam Hart, Julie Wilson () and Ian J. S. Fairlamb ()
Additional contact information
George E. Clarke: University of York
James D. Firth: University of York
Lyndsay A. Ledingham: University of York
Chris S. Horbaczewskyj: University of York
Richard A. Bourne: University of Leeds
Joshua T. W. Bray: University of York
Poppy L. Martin: University of York
Jonathan B. Eastwood: University of York
Rebecca Campbell: University of York
Alex Pagett: University of York
Duncan J. MacQuarrie: University of York
John M. Slattery: University of York
Jason M. Lynam: University of York
Adrian C. Whitwood: University of York
Jessica Milani: University of York
Sam Hart: University of York
Julie Wilson: University of York
Ian J. S. Fairlamb: University of York

Nature Communications, 2024, vol. 15, issue 1, 1-15

Abstract: Abstract Understanding complex reaction systems is critical in chemistry. While synthetic methods for selective formation of products are sought after, oftentimes it is the full reaction signature, i.e., complete profile of products/side-products, that informs mechanistic rationale and accelerates discovery chemistry. Here, we report a methodology using high-throughput experimentation and multivariate data analysis to examine the full signature of one of the most complicated chemical reactions catalyzed by palladium known in the chemical literature. A model Pd-catalyzed reaction was selected involving functionalization of 2-bromo-N-phenylbenzamide and multiple bond activation pathways. Principal component analysis, correspondence analysis and heatmaps with hierarchical clustering reveal the factors contributing to the variance in product distributions and show associations between solvents and reaction products. Using robust data from experiments performed with eight solvents, for four different reaction times at five different temperatures, we correlate side-products to a major dominant N-phenyl phenanthridinone product, and many other side products.

Date: 2024
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DOI: 10.1038/s41467-024-47939-5

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