ArticleJournal of the American Chemical Society2015
Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Modular and Stereoselective Synthesis of Cyclobutane β-Amino Alcohols.Angewandte Chemie (International ed. in English) · 2026Article
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.Chemical science · 2026Article
- Taming boroloborinines: toward photostable polycyclic antiaromatic hydrocarbons.Chemical science · 2026Article
- Positional Isomerization of 1,2-Azaborine through BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Core diversification using 1,2-oxaborines as a versatile molecular platform.Nature chemistry · 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
- Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.Organic process research & development · 2022Review
- 1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs.The Journal of organic chemistry · 2021Article
- 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
- Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes.Angewandte Chemie (International ed. in English) · 2020Article
- Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.Angewandte Chemie (International ed. in English) · 2019Article
- Late-stage functionalization of BN-heterocycles.Chemical Society reviews · 2019Article
- 1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.Journal of the American Chemical Society · 2019Article
- Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.Chemical science · 2019Article
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Abstract
The compatibility of the Negishi cross-coupling reaction with the versatile B-Cl functionality has been demonstrated in the context of late-stage functionalization of 1,2-azaborines. Alkyl-, aryl-, and alkenylzinc reagents have been utilized for the functionalization of the triply orthogonal precursor 3-bromo-1-(tert-butyldimethylsilyl)-2-chloro-1,2-dihydro-1,2-azaborine (2) to furnish new 2,3-substituted monocyclic 1,2-azaborines. This methodology has enabled the synthesis of previously elusive BN-naphthalene and BN-indenyl structures from a common intermediate.
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