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

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‐pr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-08, Vol.62 (31), p.e202305088-n/a
Main Authors: Liu, Qiang, Zhang, Bei‐Bei, Sheng, He, Qiao, Sen, Wang, Zhi‐Xiang, Chen, Xiang‐Yu
Format: Article
Language:English
Subjects:
Acetic acid
Boron
Carbon
Carborane
Carboranes
Cascade chemical reactions
Charge transfer
Charge-Transfer Complex
Electron transfer
Hybrids
Irradiation
Light irradiation
Oxindoles
Pharmaceuticals
Photochemistry
Photoreduction
Potassium
Potassium acetate
Radicals
Salts
Transition metals
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Summary: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. The photoreduction of carborane phosphonium salts, enabled by a visible‐light‐induced charge‐transfer complex, has been developed. This strategy allows access to various carborane‐oxindole‐pharmaceuticals via carbon‐centered carboranyl radicals in the absence of a transition metal (TM) and photocatalyst (PC).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202305088