Curate this paper into an ORD dataset

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

• Paper: A Validated “Pool and Split” Approach to Screening and Optimization of Copper-Catalyzed C–N Cross-Coupling Reactions
• Authors: Raphael R. Steimbach, Philipp Kollmus, Marco Santagostino
• Published: JOC, 2020-12-31
• DOI: 10.1021/acs.joc.0c02392
• 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 Cu-catalysed C-N cross-coupling screening that uses pooled copper sources, ligands and bases followed by deconvolution (JOC 2020, Boehringer Ingelheim). The SI PDF is on the ACS figshare mirror, labelled CC BY-NC 4.0. It contains DoE experimental matrices with HPLC assay% that can be extracted as text: FFD with 10 runs, CCD with 20 runs over two reaction blocks, and replicated full factorial with 32 runs. The pool-and-split screening data are shown as a scatter plot in the SI and in the main article, which is paywalled. The second SI file is a VBA HPLC-export script, not data. Pitfalls: assay% is HPLC area-based; some side products are reported in mAU, not %; compound numbers refer to structures drawn in the main article; pooled wells contain several catalysts, ligands and bases at once.

Known locations:

• https://acs.figshare.com/articles/journal_contribution/A_Validated_Pool_and_Split_Approach_to_Screening_and_Optimization_of_Copper-Catalyzed_C_N_Cross-Coupling_Reactions/13507771: SI PDF jo0c02392_si_001.pdf (24 pp): scatter plot of pool-and-split results, HPLC traces, DoE experimental matrices with assay% (FFD for 4-bromoanisole + N-benzylmethylamine; CCD for 5-bromo-1H-indole + N-benzylmethylamine; full factorial for tert-butyl carbazate + iodopyridine), NMR spectra (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)
• https://acs.figshare.com/articles/dataset/A_Validated_Pool_and_Split_Approach_to_Screening_and_Optimization_of_Copper-Catalyzed_C_N_Cross-Coupling_Reactions/13507774: jo0c02392_si_002.txt, a VBA script for exporting HPLC data (not reaction data) (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)
• https://doi.org/10.1021/acs.joc.0c02392: Article (JOC 2020) with the pool-and-split screening design, pools and main results (license: closed (ACS))

Pitfalls

Pooled screening wells contain mixtures of Cu sources, ligands and bases, so multiple catalyst/ligand components must go into one reaction. DoE factors are recorded in coded and real units. Outcomes are HPLC assay% (area-based), with some side-product values in mAU. Structures are identified by compound number and must be resolved against the main article. The scatter-plot screening data may be only partly recoverable.

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.