What can reaction databases teach us about Buchwald-Hartwig cross-couplings?
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
28 Dec 2020
28 Dec 2020
Historique:
received:
25
07
2020
accepted:
19
10
2020
entrez:
3
9
2021
pubmed:
4
9
2021
medline:
4
9
2021
Statut:
epublish
Résumé
Despite the widespread and increasing usage of Pd-catalyzed C-N cross couplings, finding good conditions for these reactions can be challenging. Practitioners mostly rely on few methodology studies or anecdotal experience. This is surprising, since the advent of data-driven experimentation and the large amount of knowledge in databases allow for data-driven insight. In this work, we address this by analyzing more than 62 000 Buchwald-Hartwig couplings gathered from CAS, Reaxys and the USPTO. Our meta-analysis of the reaction performance generates data-driven cheatsheets for reaction condition recommendation. It also provides an interactive tool to find rarer ligands with optimal performance regarding user-selected substrate properties. With this we give practitioners promising starting points. Furthermore, we study bias and diversity in the literature and summarize the current state of the reaction data, including its pitfalls. Hence, this work will also be useful for future data-driven developments such as the optimization of reaction conditions
Identifiants
pubmed: 34476050
doi: 10.1039/d0sc04074f
pii: d0sc04074f
pmc: PMC8378852
doi:
Banques de données
figshare
['10.6084/m9.figshare.5104873.v1']
Types de publication
Journal Article
Langues
eng
Pagination
13085-13093Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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