One-pot propagation of (Hetero)Arylamines: Modular synthesis of diverse Amino-di(hetero)arylamines

Liang, Xueting; Xu, Liang; Li, Cuihua; Jia, Xin; Yu, Wu

doi:10.1016/j.tet.2018.12.035

Cited by 4 publications

(1 citation statement)

References 38 publications

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“…Protecting of the boronyl groups in organoboron compounds is very important to solve this problem, but such protecting groups have not yet been discovered (Figure 2A‐2). Recent progress of this area is amination with nitro‐ArX [13] (Figure 2B‐1) and chemoselective amination [14] (Figure 2B‐2). However, the former is not an iterative amination but one of the organic synthetic methods for arranging arylamines, while the latter is a chemoselective reaction of aryl dihalides.…”

Section: Introductionmentioning

confidence: 99%

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Nojiri,

Tsuchiya,

Nishikata

2024

Chemistry A European J

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In this study, we found that the sterically bulky α‐hydroxycarboxamide moiety is a suitable framework for protecting the boronyl group of boron reagents during aminations. Condensation of α‐hydroxycarboxamide with ArB(OH)2 produced aryloxazaborolidinone (ArOxB). The reactivity of the C‐B bond in ArOxB is easily controlled by the steric and weak electronic effects of the backbone. H2N‐(or Br‐)ArOxB underwent Chan‐Evans‐Lam (C‐E‐L) or Buchwald‐Hartwig (B‐H) amination with retaining the C‐B bond. On the other hand, direct C‐E‐L amination of ArOxB was also possible in an oxidative atmosphere, in which the C‐B bond was activated by CuII species. Our methodology is effective for the precise synthesis of two or more arylamino group substituted arenes.

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Section: Introductionmentioning

confidence: 99%

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Nojiri,

Tsuchiya,

Nishikata

2024

Chemistry A European J

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Chitosan nanoparticles functionalized poly‐2‐hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N‐arylation of amines with phenylboronic acid at ambient temperature

Seyedi

Zahedifar

2021

Applied Organom Chemis

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The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan-Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs.Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan-Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance.Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan-Lam coupling reaction.

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Gradient oxygen-injecting MoS2 nanosheets catalyst boosting reductive C-N coupling of nitroarenes: Mechanistic insight into activity reconstruction

Dong

Yuan

Aizudin

et al. 2023

Applied Surface Science

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One-pot propagation of (Hetero)Arylamines: Modular synthesis of diverse Amino-di(hetero)arylamines

Cited by 4 publications

References 38 publications

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Sterically Congested Protecting Group for a Boronyl Group in Iterative Aminations

Chitosan nanoparticles functionalized poly‐2‐hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N‐arylation of amines with phenylboronic acid at ambient temperature

Gradient oxygen-injecting MoS2 nanosheets catalyst boosting reductive C-N coupling of nitroarenes: Mechanistic insight into activity reconstruction

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