ArticleNature communications2020
Regioselective functionalization of aryl azoles as powerful tool for the synthesis of pharmaceutically relevant targets.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Alkali-metal alkoxides as additives in polar organometallic chemistry for M-H and M-X exchange reactions.Chemical Society reviews · 2026Review
- The Versatile and StrategicChemical reviews · 2024Review
- Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach.Nature communications · 2022Article
- Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBuAngewandte Chemie (International ed. in English) · 2022Article
- Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Direct Preparation ofThe Journal of organic chemistry · 2021Article
- Directed regioselectiveChemical science · 2021Article
- Preparation and reactions of polyfunctional magnesium and zinc organometallics in organic synthesis.Chemical science · 2021Review
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Authors and funding
7 authors.
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Abstract
Aryl azole scaffolds are present in a wide range of pharmaceutically relevant molecules. Their ortho-selective metalation at the aryl ring is challenging, due to the competitive metalation of the more acidic heterocycle. Seeking a practical access to a key Active Pharmaceutical Ingredient (API) intermediate currently in development, we investigated the metalation of 1-aryl-1H-1,2,3-triazoles and other related heterocycles with sterically hindered metal-amide bases. We report here a room temperature and highly regioselective ortho-magnesiation of several aryl azoles using a tailored magnesium amide, TMPMgBu (TMP = 2,2,6,6-tetramethylpiperidyl) in hydrocarbon solvents followed by an efficient Pd-catalyzed arylation. This scalable and selective reaction allows variation of the initial substitution pattern of the aryl ring, the nature of the azole moiety, as well as the nature of the electrophile. This versatile method can be applied to the synthesis of bioactive azole derivatives and complements existing metal-mediated ortho-functionalizations.
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