Journal Article10.1002/ANIE.202109849
Direct, Site-Selective and Redox-Neutral α-C−H Bond Functionalization of Tetrahydrofurans via Quantum Dots Photocatalysis
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TL;DR: In this article, a semiconductor quantum dot (QD) conjugate of tetrahydrofuran (THF) was demonstrated to activate α-C-H bond of THF via forming QDs/THF conjugates.
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Abstract: As one of the most ubiquitous bulk reagents available, the intrinsic chemical inertness of tetrahydrofuran (THF) makes direct and site-selective C(sp 3 )-H bond activation difficult, especially under redox neutral condition. Here, we demonstrate that semiconductor quantum dots (QDs) can activate α-C-H bond of THF via forming QDs/THF conjugates. Under visible light irradiation, the resultant alkoxyalkyl radical directly engages in radical cross-coupling with α-amino radical from amino C-H bonds or radical addition with alkene or phenylacetylene, respectively. In contrast to stoichiometric oxidant or hydrogen atom transfer reagents required in previous studies, the scalable benchtop approach can execute α-C-H bond functionalization of THF only by a QD photocatalyst under redox-neutral condition, thus providing a broad of value added chemicals starting from bulk THFs reagent. The high step- and atom-economy, high efficiency and broad substrate scope make the photocatalysis with QDs and visible light promising in both academic and industrial setting.
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Citations
CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes.
Jonas K. Widness,Daniel G. Enny,Kaelyn S McFarlane-Connelly,Mahilet T Miedenbauer,Todd D. Krauss,Daniel J. Weix +5 more
TL;DR: In this paper , the ability of CdS nanocrystal quantum dots (QDs) to function as strong photoreductants was investigated and it was shown that Auger recombination, a photophysical phenomenon known to occur in photoexcited anionic QDs, generates transient thermally excited electrons to enable the observed reductions.
A Unique Fe–N4 Coordination System Enabling Transformation of Oxygen into Superoxide for Photocatalytic CH Activation with High Efficiency and Selectivity
Xu Xiao,Zhoushilin Ruan,Qi Li,LiPing Zhang,Hui-min Meng,Qun Zhang,Hongliang Bao,Baojiang Jiang,Jing Zhou,Chuanyu Guo,Xiaolei Wang,Honggang Fu +11 more
TL;DR: In this article , the formation of individual Fe atoms on polymeric carbon nitride (CN), that activates O2 to create O2•− for facilitating the reaction of ethylbenzene to form acetophenone, is demonstrated.
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Solvent‐in‐Gas System for Promoted Photocatalytic Ammonia Synthesis on Porous Framework Materials
Sisi Liu,Mengfan Wang,Haoqing Ji,Lifang Zhang,Jiajie Ni,Najun Li,Tao Qian,Chenglin Yan,Jianmei Lu +8 more
TL;DR: In this paper , porous framework materials are combined with a novel solvent-in-gas system, which can bring their superiority into full play, enabling photocatalysts to directly operate in a gas-dominated environment with a limited proton source uniformly suspended in it, achieving the accumulation of high concentrated nitrogen within porous framework while efficiently restricting the solvent-photocatalyst contact.
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Reductive Carbon-Carbon Coupling on Metal Sites Regulates Photocatalytic CO2 Reduction in Water Using ZnSe Quantum Dots.
TL;DR: In this paper , the first example of introducing reductive carbon-carbon (C-C) coupling reaction to block the competing H 2 evolution in photocatalytic CO 2 reduction in water was described.
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Semiconductor quantum dots: a versatile platform for photoredox organic transformation
TL;DR: Semiconductor quantum dots (QDs) are a new material with great promise in the artificial photosystems, generally exhibit attractive photoactivity and selectivity in organic photoredox transformation thanks to the tunable redox as mentioned in this paper .
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