Curate this paper into an ORD dataset

Build an Open Reaction Database (ORD) dataset of the reactions reported in:

• Paper: A “Pool and Split” Approach to the Optimization of Challenging Pd-Catalyzed C–N Cross-Coupling Reactions
• Authors: James M. Fordham, Philipp Kollmus, Monika Cavegn et al.
• Published: JOC, 2022-03-10
• DOI: 10.1021/acs.joc.2c00104
• ORD wishlist card: open on GitHub

The reference input card holds these facts, the source-data locations and the notes below in machine-readable form.

Scope

Every reaction the paper reports with its data: inputs with amounts and roles, conditions, workups, outcomes and provenance, following the ord-curation Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.

Source data

This paper describes a pool-and-split screening approach (pooled Pd/Ni precatalysts, ligand pools and bases, then deconvolution) for challenging Pd-catalysed C-N couplings (JOC 2022, Boehringer Ingelheim). The data are in the SI (ACS figshare mirror, labelled CC BY-NC 4.0), but results are shown as Spotfire pie-chart images with assay yields in the centre of each chart. ORD judged this very difficult to extract, and a spreadsheet from the authors is likely needed. Pitfalls: pooled wells contain several precatalysts and ligands (LP1-LP4 pools); conditions differ between discovery and deconvolution steps; some screens are Ni rather than Pd; outcomes are assay yields.

Known locations:

• https://acs.figshare.com/articles/journal_contribution/A_Pool_and_Split_Approach_to_the_Optimization_of_Challenging_Pd-Catalyzed_C_N_Cross-Coupling_Reactions/19335825: SI PDF jo2c00104_si_001.pdf (23 pp): Ni and Pd pool-and-split workflows shown as Spotfire pie charts (assay yields in chart centres), group Buchwald-Hartwig data overview, spectra (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)
• https://doi.org/10.1021/acs.joc.2c00104: Article (JOC 2022) with the main pool-and-split schemes and results (license: closed (ACS))

Pitfalls

Values come from images of pie charts. Pooled catalyst/ligand mixtures need multiple components per reaction. Several screening stages (discovery, deconvolution, solvent/base optimisation) use different conditions. Structures are given by compound number and must be resolved against the paywalled main text.

Deliver

• dataset: the ORD Dataset, compressed (.binpb.gz, .pb.gz, .txtpb.gz, .pbtxt.gz or .parquet), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.
• sources: a .zip with a README.md (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and validation.txt, the output of ORD's validator (ord-schema 0.8.3) on the dataset file.

Before you start

Open the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.