Literature DB >> 30844125

Concise Synthesis of Potassium Acyltrifluoroborates from Aldehydes through Copper(I)-Catalyzed Borylation/Oxidation.

Jumpei Taguchi1, Takumi Takeuchi1, Rina Takahashi1, Fabio Masero2, Hajime Ito1,3.   

Abstract

Potassium acyltrifluoroborates (KATs) were prepared through copper(I)-catalyzed borylation of aldehydes and subsequent oxidation. This synthetic route is characterized by the wide range of aldehydes accessible, favorable step economy, mild reaction conditions, and tolerance of various functional groups, and it enables the facile generation of a range of KATs, for example, bearing halide, sulfide, acetal, or ester moieties. Moreover, this method was applied to the three-step synthesis of various α-amino acid analogues that bear a KAT moiety on the C-terminus by using naturally occurring amino acids as the starting material.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  acylboron compounds; amino acids; boron; copper; oxidation

Year:  2019        PMID: 30844125     DOI: 10.1002/anie.201901748

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

Authors:  Lucia Wang; Shengjia Lin; Yawei Zhu; Daniel Ferrante; Timaf Ishak; Yuki Baba; Abhishek Sharma
Journal:  Chem Commun (Camb)       Date:  2021-04-12       Impact factor: 6.222

2.  Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.

Authors:  Xiaolei Zhang; Alexandra Friedrich; Todd B Marder
Journal:  Chemistry       Date:  2022-06-13       Impact factor: 5.020

3.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

Authors:  Shengjia Lin; Lucia Wang; Abhishek Sharma
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

4.  Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs).

Authors:  Anne Schuhmacher; Tomoya Shiro; Sarah J Ryan; Jeffrey W Bode
Journal:  Chem Sci       Date:  2020-03-10       Impact factor: 9.825

Review 5.  Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis.

Authors:  Kaijin Lin; Ang Shi; Chunhong Shi; Jinbiao Lin; Honggui Lin
Journal:  Front Chem       Date:  2021-06-23       Impact factor: 5.221

  5 in total

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