Curate this paper into an ORD dataset

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

• Paper: Palladium-Catalyzed Nitromethylation of Aryl Halides: An Orthogonal Formylation Equivalent
• Authors: Ryan R. Walvoord, Simon Berritt, Marisa C. Kozlowski
• Published: Org Lett, 2012-08-17
• DOI: 10.1021/ol301713j
• 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 304 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

Pd-catalyzed cross-coupling of aryl halides with nitromethane (Pd2dba3, 80 C). The initial parallel microscale screen used p-bromoanisole with 19 ligands x 4 solvents x 4 bases (304 conditions). Optimized conditions: Pd2dba3/XPhos, Cs2CO3, 3 A molecular sieves, 0.1 M in nitromethane. A free author manuscript is on PMC (PMC3430980). It reports only the top 8 screen results (product and impurity ratios to internal standard) and a 19-substrate isolated-yield scope table. The ORD curator found that the full screen data are not in the SI. The SI description mentions additional microscale data, so check it before concluding. The full 304-well results may need to be requested from the corresponding author. Cite DOI 10.1021/ol301713j.

Known locations:

• https://pmc.ncbi.nlm.nih.gov/articles/PMC3430980/: NIH author manuscript: Table 1 top-8 screen results (prod/IS, impurities/IS), Table 2 substrate scope (19 entries, isolated yields); screen design described in text (license: NIH public-access author manuscript; no CC license (article copyright ACS))
• https://pmc.ncbi.nlm.nih.gov/articles/instance/3430980/bin/NIHMS397383-supplement-1_si_001.pdf: SI PDF. Listed on PMC; direct fetch returned a bot-check page, so it was not inspected. The article says the SI includes 'additional parallel microscale experimentation data' (license: unknown)
• https://doi.org/10.1021/ol301713j: ACS version of record plus SI (license: ACS standard (no Crossref license entry))

Pitfalls

Screen outcomes are ratios to an internal standard (prod/IS, impurities/IS), not yields. Without the full screen, only a partial dataset (8 screen rows + 19 scope reactions) is possible from public sources. Scope substrates are drawn in Table 2, not named.

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.