Dataset Information

Metal-free synthesis of C2-quaternary indolinones by (NH₄)₂S₂O₈ mediated oxidative dearomatization of indoles.

ABSTRACT: An efficient metal-free, (NH₄)₂S₂O₈ mediated oxidative dearomatization of indoles for the construction of C2-quaternary indolinones was disclosed. A series of C2-quaternary indolinones derivatives with good functional group tolerance were obtained in moderate to excellent yields. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C2 position of indoles. This catalytic approach represents a step-economic and convenient strategy for the oxidative dearomatization of indoles.

SUBMITTER: Dong Y

PROVIDER: S-EPMC9301541 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Metal-free synthesis of C2-quaternary indolinones by (NH4)2S2O8 mediated oxidative dearomatization of indoles.

Dong Yu Y Qian Jun-Hu JH Chen Xiang-Long XL Jiang Hui H Li Xue X Zhou Qiang Q Mei Ting T Shi Zhi-Chuan ZC Li Zhong-Hui ZH He Bing B

RSC advances 20220721 33

An efficient metal-free, (NH4)2S2O8 mediated oxidative dearomatization of indoles for the construction of C2-quaternary indolinones was disclosed. A series of C2-quaternary indolinones derivatives with good functional group tolerance were obtained in moderate to excellent yields. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C2 position of indoles. This catalytic approach represents ...[more]

PMID: 35919833

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Project description:The intense research activities on the hybrid organic-inorganic perovskites (HOIPs) have led to the greatly improved light absorbers for solar cells with high power conversion efficiency (PCE). However, it is still challenging to find an alternative lead-free perovskite to replace the organohalide lead perovskites to achieve high PCE. This is because both previous experimental and theoretical investigations have shown that the Pb2+ cations play a dominating role in contributing the desirable frontier electronic bands of the HOIPs for light absorbing. Recent advances in the chemical synthesis of three-dimensional (3D) metal-free perovskites, by replacing Pb2+ with NH4 +, have markedly enriched the family of multifunctionalized perovskites (Ye et al., Science2018, 361, 151-155). These metal-free perovskites possess the chemical formula of A(NH4)X3, where A is divalent organic cations and X denotes halogen atoms. Without involving transition-metal cations, the metal-free A(NH4)X3 perovskites can entail notably different frontier electronic band features from those of the organohalide lead perovskites. Indeed, the valence and conduction bands of A(NH4)X3 perovskites are mainly attributed by the halogen atoms and the divalent A2+ organic cations, respectively. Importantly, a linear relationship between the bandgaps of A(NH4)X3 perovskites and the lowest unoccupied molecular orbital energies of the A2+ cations is identified, suggesting that bandgaps can be tailored via molecular design, especially through a chemical modification of the A2+ cations. Our comprehensive computational study and molecular design predict a metal-free perovskite, namely, 6-ammonio-1-methyl-5-nitropyrimidin-1-ium-(NH4)I3, with a desirable bandgap of ∼1.74 eV and good optical absorption property, both being important requirements for photovoltaic applications. Moreover, the application of strain can further fine-tune the bandgap of this metal-free perovskite. Our proposed design principle not only offers chemical insights into the structure-property relationship of the multifunctional metal-free perovskites but also can facilitate the discovery of highly efficient alternative, lead-free perovskites for potential photovoltaic or optoelectronic applications.

Dataset Information

Metal-free synthesis of C2-quaternary indolinones by (NH₄)₂S₂O₈ mediated oxidative dearomatization of indoles.

Publications

Metal-free synthesis of C2-quaternary indolinones by (NH<sub>4</sub>)<sub>2</sub>S<sub>2</sub>O<sub>8</sub> mediated oxidative dearomatization of indoles.

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