Direct and site-selective Pd(<scp>ii</scp>)-catalyzed C-7 arylation of indolines with arylsilanes

Luo, Haiqing; Liu, Haidong; Zhang, Zhipeng; Xiao, Yifan; Wang, Sihui; Luo, Xubiao; Wang, Kejun

doi:10.1039/c6ra06915k

Cited by 37 publications

(9 citation statements)

References 53 publications

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“…In this report, the LODs of Fe(III) and Cu(II) sensors were 1.70 × 10 −7 and 1.59 × 10 −7 [ m ], respectively, at signal/noise = 3, which were much lower than those of recently reported sensors (Figure S16a,b, Supporting Information). [ 57–61 ] Moreover, competitive experiments were completed at 55 × 10 −3 [ m ] metal ion to envisage selectivity of P1 and P2 towards Fe(III) and Cu(II), respectively. The effect of emission quenching in other metal ion solution + Fe(III)/Cu(II) was negligible than the individual Fe(III)/Cu(II) solution (Figure S16c,d, Supporting Information).…”

Section: Terpolymer Ex Situ Monomers X1a) [Mol] X2b) [Mol] X3c) [Mmolmentioning

confidence: 99%

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Dutta

Mahapatra

Deb

et al. 2020

Macromol. Rapid Commun.

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This work reports the design and synthesis of two nonaromatic biocompatible macromolecular luminogens, i.e., 2‐(dimethylamino)ethyl methacrylate‐co‐2‐(dimethylamino)ethyl 3‐(N‐(methylol)acrylamido)‐2‐methylpropanoate‐co‐N‐(methylol)acrylamide/DMAEMA‐co‐DMAENMAMP‐co‐NMA (P1) and methacrylic acid‐co‐3‐(N‐(methylol)acrylamido)‐2‐methylpropanoic acid‐co‐N‐(methylol)acrylamide/MEA‐co‐NMAMPA‐co‐NMA (P2), prepared through in situ anchored acrylamido‐ester/DMAENMAMP and acrylamido‐acid/NMAMPA third comonomers, respectively, in a facile polymerization of two non‐luminous monomers in water medium to circumvent the drawbacks related to aggregation‐caused quenching of aromatic luminogens. The structures of P1/P2, in situ anchored comonomers, fluorophores, N‐branching associated n–π* interactions, and hydrogen bonding assisted aggregation‐enhanced emissions are comprehended by nuclear magnetic resonance, Fourier transform infrared (FTIR), X‐ray photoelectron spectroscopy (XPS), ultraviolet‐visible, thermogravimetric analysis (TGA), dynamic light scattering (DLS), transmission electron microscopy (TEM), fluorescence lifetime, and fluorescence imaging. P1 and P2 are appropriate for sensitive detections/exclusions of Fe(III)/Cu(II) and cell‐imaging. The intrinsic fluorescence, on‐off sensing, selective coordinations of Fe(III) and Cu(II) with fluorophores, emission quenching mechanisms, and removals of Fe(III) and Cu(II) are investigated by DFT/NTO analyses of P1/P2 and Fe(III)‐P1 and Cu(II)‐P2 complexes, XPS, and isotherms and kinetics parameters. The excellent biocompatibilities, comparable limit of detections, i.e., 1.70 × 10−7 and 1.59 × 10−7 [m], and higher adsorption capacities, i.e., 77.25 and 154.13 mg g−1, at low ppm; 303 K; and pH = 7 compel P1/P2 to be acceptable for multipurpose applications.

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Section: Terpolymer Ex Situ Monomers X1a) [Mol] X2b) [Mol] X3c) [Mmolmentioning

confidence: 99%

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Dutta

Mahapatra

Deb

et al. 2020

Macromol. Rapid Commun.

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“…Significant effort has been dedicated to silicon-based cross-coupling reactions via C–H activation and functionalization strategy . However, these methods largely depend on the use of precious transition-metal catalysts, such as Pd, Rh, Ru, and Ir . In contrast, earth-abundant, environmentally benign first-row transition-metal-catalyzed C–H bond functionalization with readily available organosilicon reagents as coupling partners has met with very limited success in terms of catalytic efficiency and substrate scope (Scheme ).…”

mentioning

confidence: 99%

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp²)–H Bonds Enabled by Cobalt Catalysis

Ding

Shao

et al. 2020

Org. Lett.

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We report a chelation-assisted C−H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

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“…Similar to the above‐described work from Shi (Scheme ), N ‐benzoylindoline, which contains a benzanilide core, was found to react with trimethoxyphenylsilane under palladium catalysis leading to a C−H bond arylation with anilide site‐selectivity (Scheme ) . This time, the catalysis was performed with THF as the solvent and a milder temperature of 40 °C, although the loading of palladium pre‐catalyst was doubled.…”

Section: C−c Bond‐forming Reactionsmentioning

confidence: 75%

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Gramage‐Doria

2020

Chemistry A European J

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SelectiveC ÀHb ond functionalization catalyzed by metal complexes have completely revolutionized the wayi n which chemical synthesis is conceived nowadays. Typically, the reactivityo fat ransitionm etal catalyst is the key to control the site-, regio-and/or stereo-selectivity of aC ÀHb ond functionalization. Of particulari nterests are molecules that contain multiple CÀHb onds prone to undergo CÀHb ond activations with very similar bond dissociation energies at different positions. This is the case of benzanilides, relevant chemical motifs that are found in many useful fine chemicals, in which two CÀHs ites are present in chemically different aromatic fragments. In the last years, it has been found that depending on the metal catalyst and the reaction conditions, the amide motif might behave as ad irecting group towardst he metal-catalyzed CÀHb ond activation in the benzamide site or in the anilides ite. The impact and the consequences of such subtle control of site-selectivity are herein reviewed with important applicationsi ncarboncarbon and carbon-heteroatomb ond forming processes. The mechanisms unraveling these unique transformations are discussed in order to provide ab etter understanding for future developmentsi nt he field of site-selective CÀHb ond functionalization with transition metal catalysts.

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Direct and site-selective Pd(ii)-catalyzed C-7 arylation of indolines with arylsilanes

Cited by 37 publications

References 53 publications

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp²)–H Bonds Enabled by Cobalt Catalysis

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

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Direct and site-selective Pd(ii)-catalyzed C-7 arylation of indolines with arylsilanes

Cited by 37 publications

References 53 publications

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Nonconjugated Biocompatible Macromolecular Luminogens for Sensing and Removals of Fe(III) and Cu(II): DFT Studies on Selective Coordination(s) and On‐Off Sensing

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)–H Bonds Enabled by Cobalt Catalysis

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

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Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp²)–H Bonds Enabled by Cobalt Catalysis