Ausgewählte Kupfer‐katalysierte Reaktionen für die Bildung von C‐N‐, C‐O‐, C‐S‐ und C‐C‐Bindungen

Bhunia, Subhajit; Pawar, Govind Goroba; Kumar, Santosh; Jiang, Yongwen; Ma, Dawei

doi:10.1002/ange.201701690

Cited by 94 publications

(3 citation statements)

References 304 publications

(244 reference statements)

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“…Actually, among established methods, copper-mediated C-N bond formation such as Ullmann coupling plays a unique role. 10 However, the elevated reaction temperature and harsh conditions in traditional Ullmann reaction still limit its broad application. Alternatively, the combination of light and copper catalysis has opened a new arena to construct C-N bonds under milder conditions.…”

Section: Carbon-nitrogen Redox Coupling Reactionsmentioning

confidence: 99%

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Xiong

Xiao

et al. 2021

Synthesis

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In recent years, visible-light-mediated copper photocatalysis have emerged as an attractive strategy for the diverse constructions of basic bonds in an ecologically benign and cost-effective fashion. The intense activity and increasing work of these areas stimulated the exploit of the distinctive properties of copper photocatalysis and the rapid development and expansion of their applications. In this review, we focus on introducing a series of significant achievements in copper complexes as standalone photocatalysis in organic reactions to make an attempt to exhibit their potential capabilities and high flexibilities in synthetic chemistry.

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Section: Carbon-nitrogen Redox Coupling Reactionsmentioning

confidence: 99%

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Xiong

Xiao

et al. 2021

Synthesis

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“…The prevalence of Cu-catalyzed cross-coupling reactions involving aryl and nitrogenous heterocycles is irrefutable in the domain of N -arylation chemistry . Two major synthetic protocols have been used for decades for these C–N cross-couplings: Chan–Evans–Lam (CEL) type, where both the aryl and amine parts are nucleophilic, and Ullmann pathway, where electrophilic aryls couple with nucleophilic N -heterocycles .…”

Section: Introductionmentioning

confidence: 99%

7-Azaindole N-Oxide (7-AINO) Mediated Cu-Catalyzed N-Arylation: Mechanistic Investigation into the Role of Fluoride Ions

Mondal,

Mukhopadhyay,

Patra

et al. 2023

ACS Catal.

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A Cu(II) fluoride-catalyzed N-arylation of 7-azaindole N-oxides (7-AINO) has been developed using boronic acid under base-free conditions. During the process, a combination of spectroscopy and crystallography techniques has identified the exact formulation of key reaction intermediates that allowed to propose a complete mechanistic description establishing the role of 7-AINO as a ligand and deducing the crucial role of fluoride ions (F–) in the entire catalytic cycle. A monomeric Cu(II)-7-AINO complex (4) has been detected as a reaction intermediate along with isolation of its dimeric analog (4a) and confirmed by X-ray analysis and mass spectroscopy. The subsequent conversion of Cu(II)-7-AINO complex (4/4a) to catalytically active monomeric fluorinated Cu(II)-complex (I) has been confirmed by 19F NMR, mass, and EPR spectroscopy, reiterating the vital role of fluoride ions in forming the active catalyst. Further, the synthesized Cu(II)-7-AINO complex (4a) in combination with TBAF has been established as an alternative catalytic system for CEL coupling, and its efficiency has been demonstrated for N-arylation of various N-containing nucleophiles. Moreover, a general attempt has been made to promote F– as complementary to the base as well as a CEL catalyst promoter. The role of 7-azaindole-N-oxide (7-AINO) as a ligand was further evaluated, where it acts as an apposite promoter for the Cu-catalyzed N-arylation of azoles in Ullmann-type coupling. The synthetic potential of this methodology is further demonstrated through the synthesis of various pharmaceutically important 7-azaindole annulated derivatives.

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“…Also importantly, because of the robust bonds by dynamic trimerization reaction, CTFs are distinguished for its excellent water resistance and chemical stability, [22] indicating their great potential for applications in harsh conditions. [24] Currently, most CTFs were used as absorbents [25][26][27][28][29][30] by taking advantages of their large surface areas, and their usages in membrane separation are rare. The main reason is that CTFs are usually synthesized as particulates and delaminating them into thin multilayers as building blocks for membranes remains a big challenge.…”

Section: Introductionmentioning

confidence: 99%

Nanofluidic Behaviors of Water and Ions in Covalent Triazine Framework (CTF) Multilayers

Wei

Zhou

et al. 2019

Small

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Covalent triazine frameworks (CTFs) hosting arrays of highly ordered sub‐2‐nm pores are expected to exhibit unusual nanofluidic behaviors, which may enable important applications such as desalination. Herein, nonequilibrium molecular dynamics simulations are applied to investigate transport of water and ions inside two typical CTFs—CTF‐1, and CTF‐2—having intrinsic pores of 1.2 and 1.5 nm, respectively. Their monolayers exhibit extremely high water permeance but weak ion rejection. CTF multilayers are then investigated. Transport resistances composed of interior and interfacial contribution are correlated with stacking numbers of CTF monolayers to develop equations of predicting water permeance. It is revealed that both the stacking fashion and the number of CTF monolayers forming multilayers significantly influence permeation and ion rejection. Staggered multilayers exhibit much higher ion rejection than eclipsed ones. Staggered CTF‐2 multilayers completely reject ions because the interlayer paths between two adjacent staggered monolayers allow only water molecules to pass through. Importantly, it is predicted from the equations that few‐layered staggered CTF‐2 multilayers, which can be relatively easily produced by experimental methods, exhibit 100% NaCl rejection and up to 100 times higher permeance than commercial reverse osmosis membranes, implying their great potential as building blocks to prepare next‐generation desalination membranes.

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Ausgewählte Kupfer‐katalysierte Reaktionen für die Bildung von C‐N‐, C‐O‐, C‐S‐ und C‐C‐Bindungen

Cited by 94 publications

References 304 publications

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

7-Azaindole N-Oxide (7-AINO) Mediated Cu-Catalyzed N-Arylation: Mechanistic Investigation into the Role of Fluoride Ions

Nanofluidic Behaviors of Water and Ions in Covalent Triazine Framework (CTF) Multilayers

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