Curate this paper into an ORD dataset

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

• Paper: Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions: A Combined Experimental and Computational Study
• Authors: Tiezheng Jia, Mengnan Zhang, Samuel P. McCollom et al.
• Published: JACS, 2017-05-24
• DOI: 10.1021/jacs.7b03623
• 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 100 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

Source: Jia et al., J. Am. Chem. Soc. 2017, doi:10.1021/jacs.7b03623. Pd-catalysed enantioselective arylation of aryl sulfenate anions, about 100 HTE reactions. The data is in the Supporting Information PDF as a table with chemical structure drawings. Every species needs SMILES assigned from the drawings, with correct stereochemistry for the chiral ligands and the S-stereogenic sulfoxide products. Record enantioselectivity (ee/er) as well as yield where given. The SI is ACS-hosted and not openly licensed. Cite it, but do not redistribute it.

Known locations:

• https://doi.org/10.1021/jacs.7b03623: JACS article landing page and ACS-hosted SI PDF (table with chemical structures) (license: ACS publisher terms (not open))
• http://hdl.handle.net/11336/51595: Green OA copy of the manuscript listed by OpenAlex (CONICET repository); the handle did not resolve when checked, and the SI is probably not included (license: cc-by-nc-sa (per OpenAlex; applies to the manuscript, not the SI))

Pitfalls

Enantioselective outcomes need ee values and stereo-defined SMILES for the chiral ligands and sulfoxide products. Structures come only as images, so reviewers must check SMILES against the drawings. The screen may vary ligand and conditions across a single template. The computational part of the paper is out of scope.

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.