Charge transfer complex enabled photoreduction of Wittig phosphonium salts

Tan, Fang; Zheng, Peng; Liu, Qiang; Chen, Xiang‐Yu

doi:10.1039/d2qo01079h

Org. Chem. Front.

2022

DOI: 10.1039/d2qo01079h

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Charge transfer complex enabled photoreduction of Wittig phosphonium salts

Fang Tan

Peng Zheng

Qiang Liu

et al.

Abstract: A photoinduced charge transfer complex strategy enabled (alkoxycarbonyl)methylation reaction of alkenes with phosphonium salts has been reported. This strategy provides a convenient strategy to functionalize indoles, 1,1-diphenylethylenes, enamides and N-phenyl...

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Cited by 10 publications

References 23 publications

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Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Liu

Zhang

et al. 2023

Angewandte Chemie

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Visible‐light‐induced photoreaction of carboranes is an effective approach to prepare carborane‐containing compounds. While several methods involving boron‐centered carboranyl radicals have been established, those for carbon‐centered carboranyl radicals are underdeveloped, except for the UV‐light‐promoted photohomolysis. Herein, we describe a simple but effective approach to access carbon‐centered carboranyl radicals by photoreduction of carborane phosphonium salts under blue light irradiation without using transition metals and photocatalysts. The utility of the method was demonstrated by successfully preparing a range of carborane‐oxindole‐pharmaceutical hybrids by radical cascade reactions. Computational and experimental studies suggest that the carbon‐centered carboranyl radicals are generated by single‐electron transfer of the photoactive charge‐transfer complexes between the salts and the additive potassium acetate.

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Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Liu

Zhang

et al. 2023

Angewandte Chemie

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show abstract

Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Liu

Zhang

et al. 2023

Angew Chem Int Ed

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Charge transfer complex enabled photoreduction of ether phosphonium salts for the selective oxyalkylation of enamides

Qiao,

Chen,

Liu

et al. 2024

Chinese Chemical Letters

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Charge transfer complex enabled photoreduction of Wittig phosphonium salts

Abstract: A photoinduced charge transfer complex strategy enabled (alkoxycarbonyl)methylation reaction of alkenes with phosphonium salts has been reported. This strategy provides a convenient strategy to functionalize indoles, 1,1-diphenylethylenes, enamides and N-phenyl...

Cited by 10 publications

References 23 publications

Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Visible‐Light‐Induced Photoreduction of Carborane Phosphonium Salts: Efficient Synthesis of Carborane‐Oxindole‐Pharmaceutical Hybrids

Charge transfer complex enabled photoreduction of ether phosphonium salts for the selective oxyalkylation of enamides

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