A machine-learning tool to predict substrate-adaptive conditions for Pd-catalyzed C–N couplings

N. Ian Rinehart, Rakesh K. Saunthwal, Joël Wellauer, Andrew F. Zahrt, Lukas Schlemper, Alexander S. Shved, Raphael Bigler, Serena Fantasia, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review

Abstract

Machine-learning methods have great potential to accelerate the identification of reaction conditions for chemical transformations. A tool that gives substrate-adaptive conditions for palladium (Pd)–catalyzed carbon-nitrogen (C–N) couplings is presented. The design and construction of this tool required the generation of an experimental dataset that explores a diverse network of reactant pairings across a set of reaction conditions. A large scope of C–N couplings was actively learned by neural network models by using a systematic process to design experiments. The models showed good performance in experimental validation: Ten products were isolated in more than 85% yield from a range of couplings with out-of-sample reactants designed to challenge the models. Importantly, the developed workflow continually improves the prediction capability of the tool as the corpus of data grows.

Original languageEnglish (US)
Pages (from-to)965-972
Number of pages8
JournalScience
Volume381
Issue number6661
DOIs
StatePublished - Sep 1 2023

ASJC Scopus subject areas

  • General

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