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Cross-Coupling Reactions of 5-Bromo-1,2,3-triazine


Hoff, Lukas V; Hauser, Joana M; Gademann, Karl (2022). Cross-Coupling Reactions of 5-Bromo-1,2,3-triazine. Journal of Organic Chemistry, 87(22):15684-15692.

Abstract

An efficient Pd catalyzed cross-coupling method for 5-bromo-1,2,3-triazine is described. Optimization of the reaction conditions allowed for the preparation of a representative scope of (hetero)aryl-1,2,3-triazines (20 examples, up to 97% yield). The reaction scope was evaluated using a data science enabled boronic acid chemical space to assess the generality of the method. Additionally, diversification of the resulting products enabled the preparation of pyrimidines and pyridines in yields of up to 80% and in only two steps.

Abstract

An efficient Pd catalyzed cross-coupling method for 5-bromo-1,2,3-triazine is described. Optimization of the reaction conditions allowed for the preparation of a representative scope of (hetero)aryl-1,2,3-triazines (20 examples, up to 97% yield). The reaction scope was evaluated using a data science enabled boronic acid chemical space to assess the generality of the method. Additionally, diversification of the resulting products enabled the preparation of pyrimidines and pyridines in yields of up to 80% and in only two steps.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry
Language:English
Date:18 November 2022
Deposited On:10 Jan 2023 13:48
Last Modified:30 Jan 2024 02:37
Publisher:American Chemical Society (ACS)
ISSN:0022-3263
Additional Information:This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/page/copyright/permissions.html.
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.joc.2c02082
PubMed ID:36305330
  • Content: Accepted Version
  • Language: English