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Mechanistic Studies and Data Science-Guided Exploration of Bromotetrazine Cross-Coupling


Hoff, Lukas V; Chesnokov, Gleb A; Linden, Anthony; Gademann, Karl (2022). Mechanistic Studies and Data Science-Guided Exploration of Bromotetrazine Cross-Coupling. ACS Catalysis, 12:9226-9237.

Abstract

A thorough mechanistic investigation of the Pd- catalyzed and Ag-mediated cross-coupling of the monosubstituted tetrazine 3-bromo-1,2,4,5-tetrazine with boronic acids is reported. The study combines kinetic analyses, isolation of catalytic intermediates, and computational methods to gain insights into the mechanism. On the basis of these experimentally validated hypotheses, a highly electron-deficient ligand was predicted to overcome the challenge of coupling previously unfeasible substrates, which in turn was confirmed experimentally. In addition, a data-driven workflow was applied to study how the mechanistic understanding impacts the generality of the scope.

Abstract

A thorough mechanistic investigation of the Pd- catalyzed and Ag-mediated cross-coupling of the monosubstituted tetrazine 3-bromo-1,2,4,5-tetrazine with boronic acids is reported. The study combines kinetic analyses, isolation of catalytic intermediates, and computational methods to gain insights into the mechanism. On the basis of these experimentally validated hypotheses, a highly electron-deficient ligand was predicted to overcome the challenge of coupling previously unfeasible substrates, which in turn was confirmed experimentally. In addition, a data-driven workflow was applied to study how the mechanistic understanding impacts the generality of the scope.

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Additional indexing

Item Type:Journal Article, not_refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Catalysis, General Chemistry
Language:English
Date:15 July 2022
Deposited On:19 Jul 2022 08:34
Last Modified:28 Mar 2024 02:37
Publisher:American Chemical Society (ACS)
ISSN:2155-5435
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acscatal.2c01813
Project Information:
  • : FunderSNSF
  • : Grant ID200021_182043
  • : Project TitleMechanism-Based Design, Synthesis, Biological Evaluation, and Delivery of Next-Generation Antibiotics