Iron-catalyzed β-hydroxymethylative carbonylation of styrene under photo-irradiation

This study describes an iron-catalyzed divergent oxidation of styrene into β-hydroxylmethylketone and ketone under photo-irradiation. This divergence is ascribed to the use of styrene with various substituents. More importantly, methanol is oxidized into formaldehyde in the reaction and serves as a...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-11, Vol.59 (89), p.1339-13312
Main Authors: Guan, Meng, Hou, Ming, Tang, Shuwang, Cheng, Guang, Zhu, Xinyu, Zhao, Yun-Hui, Tang, Ximei, Zhou, Hongwei, Qiu, Guanyinsheng
Format: Article
Language:English
Subjects:
Carbonyls
Iron
Irradiation
Ketones
Natural products
Oxidation
Styrenes
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Summary:This study describes an iron-catalyzed divergent oxidation of styrene into β-hydroxylmethylketone and ketone under photo-irradiation. This divergence is ascribed to the use of styrene with various substituents. More importantly, methanol is oxidized into formaldehyde in the reaction and serves as a C1 synthon. Mechanism investigations show that the reaction is initiated by oxidative SET to transfer styrene into the cation radical. The reaction pathway undergoes HAT and β-hydride elimination as well as a concerted cyclization. Particularly, several drug-like molecules, such as melperone analogue, lenperone analogue, and haloperidol analogue, are synthesized. In addition, this method is also applicable to the synthesis of natural product ( R )- atomoxetine . This paper describes an iron-catalyzed divergent oxidation of styrene into β-hydroxylmethylketone and ketone under photo-irradiation. The divergence is ascribed to the use of substrates with different substituents.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc03919f