ArticleJournal of the American Chemical Society2019
1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Positional Isomerization of 1,2-Azaborine through BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Mechanistic Insight into the Thermal Ring Opening of the Dewar Isomer of 1,2-Dihydro-1,2-azaborinines.JACS Au · 2025Article
- Synthesis of Chiral δ-Aminoboronic Esters by Enantioselective Hydrogenation of 1,2-Azaborines.Angewandte Chemie (International ed. in English) · 2025Article
- Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2024Article
- N-Functionalization of 1,2-Azaborines.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023Article
- The aromatic Claisen rearrangement of a 1,2-azaborine.Organic & biomolecular chemistry · 2023Article
- The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.Journal of the American Chemical Society · 2021Article
- 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
- Density Functional Studies on Photophysical Properties of Boron-Pyridyl-Imino-Isoindoline Dyes: Effect of the Fusion.ACS omega · 2020Article
- Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.Angewandte Chemie (International ed. in English) · 2019Article
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4 authors.
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Abstract
Two new 1,2-azaborine building blocks that enable the broad diversification of previously not readily accessible C4 and C5 ring positions of the 1,2-azaborine heterocycle are developed. 1,2-Azaborine's distinct electronic structure allowed the resolution of a mixture of C4- and C5-borylated 1,2-azaborines. The connection between the electronic structure of C4 and C5 positions of 1,2-azaborine and their distinct reactivity patterns is revealed by a combination of reactivity studies and kinetic measurements that are supported by DFT calculations. Specifically, we show that oxidation by N-methylmorpholine N-oxide (NMO) is selective for the C4-borylated 1,2-azaborine, and the Ir-catalyzed deborylation is selective for the C5-borylated 1,2-azaborine via kinetically controlled processes. On the other hand, ligand exchange with diethanolamine takes place selectively with the C4-borylated isomer via a thermodynamically controlled process. These results represent the first examples for chemically distinguishing a mixture of two aryl mono-Bpin-substituted isomers.
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