# Curate this paper into an ORD dataset

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

- **Paper:** High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides
- **Authors:** Joseph Becica, Damian P. Hruszkewycz, Janelle E. Steves et al.
- **Published:** Org Lett, 2019-10-25
- **DOI:** [10.1021/acs.orglett.9b03380](https://doi.org/10.1021/acs.orglett.9b03380)
- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570091)

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 336 reactions): 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

Org. Lett. 2019, 21, 8981-8986 (DOI 10.1021/acs.orglett.9b03380). A targeted high-throughput experimentation campaign (about 336 reactions) identified Pd/AdBippyPhos as a general catalyst for N-arylation of weakly nucleophilic sulfonamides to N,N-diaryl sulfonamides, with ligand steric parametrisation. The tabulated HTE data is in the Supporting Information. A preprint is on ChemRxiv (DOI 10.26434/chemrxiv.9108461.v2, CC BY-NC-ND 4.0), but whether it carries the same SI is unverified. The journal article is closed access. No machine-readable data file or SMILES is known. Ligands, precatalysts and substrates must be converted to SMILES or named identifiers. Pitfalls: HTE yields are probably assay yields (HPLC or UPLC against an internal standard) and must be labelled as such, and the ligand screen and the substrate scope should be kept distinct.

Known locations:

- [https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.9b03380](https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.9b03380): Org. Lett. 2019, 21, 8981-8986 Supporting Information (tabulated HTE data per the ORD board notes). The listing returned HTTP 403 (bot challenge). (license: ACS publisher copyright (article closed access))
- [https://doi.org/10.26434/chemrxiv.9108461.v2](https://doi.org/10.26434/chemrxiv.9108461.v2): ChemRxiv preprint of the same work (v2, posted 2019-09-06). Whether it has SI or data files is unknown because the ChemRxiv API was behind a Cloudflare challenge. (license: CC BY-NC-ND 4.0 (per Crossref))

## Pitfalls

Several ligand screens plus substrate scope. Assay versus isolated yields must be distinguished. Bulky phosphine ligands (AdBippyPhos and others) need correct SMILES or named identifiers. Some wells may report only conversion or product/internal-standard ratios.

## 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.