Photoinduced Activation of Unactivated C(<i>sp</i><sup>3</sup>)‐H Bonds and Acylation Reactions

Ren, Chen‐Chao; Wang, Tian‐Qi; Peng, Dao; Liu, Xiaoqing; Wu, Qing‐An; Liu, Xuefen; Luo, Shu‐Ping

doi:10.1002/slct.202100225

Cited by 10 publications

(18 citation statements)

References 84 publications

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“…Of note, this protocol could be applied to the manipulation of natural products (see the case of 35.5 ) . Very recently, a dual-catalytic strategy based on DCBP and a Ni-based complex enabled the construction of C(sp 3 )–C(sp 2 ) bonds via the acylation of methylbenzenes with N -acylsuccinimides …”

Section: Formation Of C–c Bondsmentioning

confidence: 99%

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

2021

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Direct photocatalyzed hydrogen atom transfer (d-HAT) can be considered a method of choice for the elaboration of aliphatic C–H bonds. In this manifold, a photocatalyst (PCHAT) exploits the energy of a photon to trigger the homolytic cleavage of such bonds in organic compounds. Selective C–H bond elaboration may be achieved by a judicious choice of the hydrogen abstractor (key parameters are the electronic character and the molecular structure), as well as reaction additives. Different are the classes of PCsHAT available, including aromatic ketones, xanthene dyes (Eosin Y), polyoxometalates, uranyl salts, a metal-oxo porphyrin and a tris(amino)cyclopropenium radical dication. The processes (mainly C–C bond formation) are in most cases carried out under mild conditions with the help of visible light. The aim of this review is to offer a comprehensive survey of the synthetic applications of photocatalyzed d-HAT.

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Section: Formation Of C–c Bondsmentioning

confidence: 99%

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

2021

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“…Key amine compound 3-amino-3-deoxy-2,5-anhydro- d -mannitol ( 7 ) was prepared from 3-azido-3-deoxy-2,5-anhydro- d -mannitol according to the reported procedure , …”

Section: Methodsmentioning

confidence: 99%

“…46 N-Hydroxy-succinimidyl dihydrocinnamate and 4-fluoro-3-nitrobenzenesulfonyl chloride were synthesized following their reported procedures. 47,48 9). Amine 7 (0.12 g, 0.73 mmol) was stirred in dry DMF (12 mL) in a 1-neck round-bottom flask under N 2 atmosphere until it was completely dissolved.…”

Section: Synthesismentioning

confidence: 99%

A Fluorescence-Based Assay to Probe Inhibitory Effect of Fructose Mimics on GLUT5 Transport in Breast Cancer Cells

Rana

Aziz

Serya

et al. 2022

ACS Bio Med Chem Au

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Rapid cell division and reprogramming of energy metabolism are two crucial hallmarks of cancer cells. In humans, hexose trafficking into cancer cells is mainly mediated through a family of glucose transporters (GLUTs), which are facilitative transmembrane hexose transporter proteins. In several breast cancers, fructose can functionally substitute glucose as an alternative energy supply supporting rapid proliferation. GLUT5, the principal fructose transporter, is overexpressed in human breast cancer cells, providing valuable targets for breast cancer detection as well as selective targeting of anticancer drugs using structurally modified fructose mimics. Herein, a novel fluorescence assay was designed aiming to screen a series of C-3 modified 2,5anhydromannitol (2,5-AM) compounds as D-fructose analogues to explore GLUT5 binding site requirements. The synthesized probes were evaluated for their ability to inhibit the uptake of the fluorescently labeled D-fructose derivative 6-NBDF into EMT6 murine breast cancer cells. A few of the compounds screened demonstrated highly potent single-digit micromolar inhibition of 6-NBDF cellular uptake, which was substantially more potent than the natural substrate D-fructose, at a level of 100-fold or more. The results of this assay are consistent with those obtained from a previous study conducted for some selected compounds against 18 F-labeled D-fructose-based probe 6-[ 18 F]FDF, indicating the reproducibility of the current non-radiolabeled assay. These highly potent compounds assessed against 6-NBDF open avenues for the development of more potent probes targeting GLUT5-expressing cancerous cells.

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“…A related process involved the conversion of toluene into 1,2-arylethanone using 4,4’-dichlorobenzophenone ( 27 ) as the photocatalyst and NiCl 2 ·DME as the nickel catalyst under UVA irradiation ( Scheme 44 ) [ 127 ]. Here, N -acylsuccinimides 84 were used as the acyl source.…”

Section: Reviewmentioning

confidence: 99%

Photoredox catalysis in nickel-catalyzed C–H functionalization

Mantry¹,

Maayuri²,

Kumar³

et al. 2021

Beilstein J. Org. Chem.

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Catalytic C‒H functionalization has become a powerful strategy in organic synthesis due to the improved atom-, step- and resource economy in comparison with cross-coupling or classical organic functional group transformations. Despite the significant advances in the metal-catalyzed C‒H activations, recent developments in the field of metallaphotoredox catalysis enabled C‒H functionalizations with unique reaction pathways under mild reaction conditions. Given the relative earth-abundance and cost-effective nature, nickel catalysts for photoredox C‒H functionalization have received significant attention. In this review, we highlight the developments in the field of photoredox nickel-catalyzed C‒H functionalization reactions with a range of applications until summer 2021.

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Photoinduced Activation of Unactivated C(sp³)‐H Bonds and Acylation Reactions

Cited by 10 publications

References 84 publications

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

A Fluorescence-Based Assay to Probe Inhibitory Effect of Fructose Mimics on GLUT5 Transport in Breast Cancer Cells

Photoredox catalysis in nickel-catalyzed C–H functionalization

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Photoinduced Activation of Unactivated C(sp3)‐H Bonds and Acylation Reactions

Cited by 10 publications

References 84 publications

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration

A Fluorescence-Based Assay to Probe Inhibitory Effect of Fructose Mimics on GLUT5 Transport in Breast Cancer Cells

Photoredox catalysis in nickel-catalyzed C–H functionalization

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Product

Resources

About

Photoinduced Activation of Unactivated C(sp³)‐H Bonds and Acylation Reactions