ArticleThe Journal of organic chemistry2017
Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C-H Activation.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Synthesis and crystal structure of bis-(9-mesityl-9,10-di-hydro-10-aza-9-borabenzo[Acta crystallographica. Section E, Crystallographic communications · 2023Article
- Selectivity in the Elaboration of Bicyclic Borazarenes.Advanced synthesis & catalysis · 2021Article
- One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids.Chemical science · 2021Article
- Iridium-Catalysed C-H Borylation of Heteroarenes: Balancing Steric and Electronic Regiocontrol.Angewandte Chemie (International ed. in English) · 2021Review
- Late-stage functionalization of BN-heterocycles.Chemical Society reviews · 2019Article
- Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.Organic letters · 2019Article
- 3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.The Journal of organic chemistry · 2018Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Methods for the regioselective C-H borylation and subsequent cross-coupling of the 2,1-borazaronaphthalene core are reported. Azaborines are dependent on B-N/C═C isosterism when employed in strategies for developing diverse heterocyclic scaffolds. Although 2,1-borazaronaphthalene is closely related to naphthalene in terms of structure, the argument is made that the former has electronic similarities to indole. Based on that premise, iridium-mediated C-H activation has enabled facile installation of a versatile, nucleophilic coupling handle at a previously inaccessible site of 2,1-borazaronaphthalenes. A variety of substituted 2,1-borazaronaphthalene cores can be successfully borylated and further cross-coupled in a facile manner to yield diverse C(8)-substituted 2,1-borazaronaphthalenes.
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Registered trials
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