ArticleChemical science2018
Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs)
Article in Chemical science, 2018. 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.
- Application of the Horner-Wadsworth-Emmons Olefination in the Construction ofThe Journal of organic chemistry · 2025Article
- Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes.Journal of the American Chemical Society · 2023Article
- Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes.ACS catalysis · 2023Article
- Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acidsChemical science · 2022Article
- Iterative addition of carbon nucleophiles toChemical science · 2021Article
- Acyl metalloids: conformity and deviation from carbonyl reactivity.Chemical science · 2021Review
- Review
- Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs).Chemical science · 2020Article
- Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products.Nature catalysis · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.
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Registered trials
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