Copper dual-atom catalyst mediated C3–H amination of indoles at room temperature

Lu, Yuanhui; Chen, Tianxiang; Xiao, Xiaoyu; Huang, Ninghua; Dou, Yadong; Wei, Wanxing; Zhang, Zhuan; Lo, Benedict T. W.; Liang, Taoyuan

doi:10.1039/d2cy01126c

Cited by 7 publications

(2 citation statements)

References 44 publications

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“…And the phenothiazine radical intermediate 63 was confirmed via ESR spectroscopy by Patureau, Lei, Knölker, and Tan groups [8d,i,k,l,9f] . The involvement of phenothiazine radical 63 should be supported as well by previous studies from Antonchick, Liu, Liang, Li, Xia, MacMillan, and other groups [8f,h,n,9d,10a–c] . Based on the above results and relevant mechanistic studies in the literature, [8–10] a possible mechanism for the amination reaction was proposed (Figure 3B).…”

Section: Resultssupporting

confidence: 62%

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

2023

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A modular protocol for the triarylamine synthesis has been developed using diarylamines and electron-rich arenes, such as phenols, as the building blocks. The KI/KIO 4 system proves to be highly efficient for the cross-dehydrogenative coupling of phenothiazines/phenoxazines with phenols/anilines. A wide range of functional groups attached to both coupling partners were well tolerated. Through the manipulation of reaction temperatures, the sequential assembly of bis-triarylamines could be achieved to provide the unsymmetrically bis-aminated phenols efficiently. Furthermore, the multiple aminated polyphenols were rapidly constructed in good to high yields by a single operation.

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Section: Resultssupporting

confidence: 62%

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

2023

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“…Interestingly, a closer analysis of the AC-HAADF STEM im-ages reveals distinguishable cooperative Cu atom sites (quasidual/triple atom sites) within the PHI/PTI matrices (circled areas in Figure 3d) that are distinct from conventional dual atom catalysts, reported previously. [86][87][88][89] DFT studies in combination with EXAFS reveal the thermodynamic feasibility of multiple Cu sites (Cu-N 2 ) within the triangular nanopores having interatomic distances of ≈4 (in 9N triazine pores) and ≈9 Å (in 15N heptazine pores) for PTI and PHI, respectively. AC-HAADF STEM imaging on Cu-PTI with low Cu ion density (Figure S7, Supporting Information) show the formation of several quasi-dual and -triple atom sites with large interatomic distances in the PTI matrix.…”

Section: Microscopic Analysismentioning

confidence: 99%

Cooperative Copper Single‐Atom Catalyst in 2D Carbon Nitride for Enhanced CO₂ Electrolysis to Methane

Roy

Chen

et al. 2024

Advanced Materials

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Renewable electricity powered carbon dioxide (CO2) reduction (eCO2R) to high‐value fuels like methane (CH4) holds the potential to close the carbon cycle at meaningful scales. However, this kinetically staggered 8‐electron multistep reduction still suffers from inadequate catalytic efficiency and current density. Atomic Cu‐structures can boost eCO2R‐to‐CH4 selectivity due to enhanced intermediate binding energies (BEs) resulting from favorably shifted d‐band centers. Herein, we exploit two‐dimensional carbon nitride (CN) matrices, viz. Na‐polyheptazine (PHI) and Li‐polytriazine imides (PTI), to host Cu‐N2 type single atom sites with high density (∼1.5 at%), via a facile metal ion exchange process. Optimized Cu loading in nanocrystalline Cu‐PTI maximizes eCO2R‐to‐CH4 performance with Faradaic efficiency (FECH4) of ≈68% and a high partial current density of 348 mA cm−2 at a low potential of ‐0.84 V versus RHE, surpassing the state‐of‐the‐art catalysts. Multi‐Cu substituted N‐appended nanopores in the CN frameworks yield thermodynamically stable quasi‐dual/triple sites with large interatomic distances dictated by the pore dimensions. First‐principles calculations elucidate the relative Cu‐CN cooperative effects between the two matrices and how the Cu‐Cu distance and local environment dictate the adsorbate BEs, density of states, and CO2‐to‐CH4 energy profile landscape. The 9N pores in Cu‐PTI yield cooperative Cu‐Cu sites that synergistically enhance the kinetics of the rate‐limiting steps in the eCO2R‐to‐CH4 pathway.This article is protected by copyright. All rights reserved

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Copper‐mediated Intermolecular C−H aminohalogenation of Indoles at Room Temperature

Zhang

Xiao

et al. 2022

Asian J Org Chem

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An efficient intermolecular CÀ H aminohalogenation of indoles with azoles and NXS (X = F, Cl, Br, I) has been developed. This mild protocol provides a straightforward entry to structurally valuable 2-azolyl-3-halogenated indoles in one single operation. In addition, this attractive route for the synthesis of polyfunctionalized indoles is of great significance due to the product's versatile reactivity for further transformations.

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Copper dual-atom catalyst mediated C3–H amination of indoles at room temperature

Abstract: An efficient zeolite supported copper dual-atom catalyst for C–H amination of indoles has been developed for the green synthesis of 3-diarylaminoindoles.

Cited by 7 publications

References 44 publications

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

Cooperative Copper Single‐Atom Catalyst in 2D Carbon Nitride for Enhanced CO₂ Electrolysis to Methane

Copper‐mediated Intermolecular C−H aminohalogenation of Indoles at Room Temperature

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Copper dual-atom catalyst mediated C3–H amination of indoles at room temperature

Abstract: An efficient zeolite supported copper dual-atom catalyst for C–H amination of indoles has been developed for the green synthesis of 3-diarylaminoindoles.

Cited by 7 publications

References 44 publications

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

Modular Synthesis of Triarylamines and Poly(triarylamine)s through a Radical Mechanism

Cooperative Copper Single‐Atom Catalyst in 2D Carbon Nitride for Enhanced CO2 Electrolysis to Methane

Copper‐mediated Intermolecular C−H aminohalogenation of Indoles at Room Temperature

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Cooperative Copper Single‐Atom Catalyst in 2D Carbon Nitride for Enhanced CO₂ Electrolysis to Methane