Curate this paper into an ORD dataset

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

• Paper: Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization
• Authors: Erik Weis, Maria C. Johansson, Maria C. Johansson et al.
• Published: JACS Au, 2022-04-13
• DOI: 10.1021/jacsau.2c00039
• 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 (the wishlist estimates about 300 reactions; HTE): 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

Ir-catalysed directed C-H amination HTE from Weis et al., JACS Au 2022 (doi:10.1021/jacsau.2c00039), an open-access CC BY 4.0 article also in PMC (PMC9088304). About 300 reactions run as single 96-well plate screens: initial condition optimisation, then a directing-group informer library of 48 substrates tested in DCE, CPME, EtOAc and NMP with [Cp*Ir(H2O)3]SO4, then late-stage functionalisation examples. Conversions, including for unproductive substrates, are reported in the Supporting Information PDF (about 17 MB). Structures are drawn, not given as SMILES, so each substrate, product and directing group must be converted to SMILES and checked. Outcomes are mostly LC conversions, with isolated yields for selected products. The ORD Dataset must cite the paper DOI.

Known locations:

• https://www.ebi.ac.uk/europepmc/webservices/rest/PMC9088304/fullTextXML: Full text (PMC9088304) under CC BY 4.0; states that the complete list of conversions, including unproductive substrates, is in the SI (license: CC-BY-4.0 (article))
• https://pmc.ncbi.nlm.nih.gov/articles/PMC9088304/: SI PDF au2c00039_si_001.pdf (about 17 MB per PMC metadata; not downloaded) with plate screens and conversion tables (license: Distributed with the CC BY 4.0 article; SI license not separately stated)
• https://doi.org/10.26434/chemrxiv-2021-vp0kl: ChemRxiv preprint (site blocked automated access) (license: unknown)

Pitfalls

Mix of screening conversions (LC area-based) and isolated yields. Structures must be transcribed from images. Plate layouts are spread across many single-plate figures. Regioisomer outcomes are reported for some substrates.

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.