A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical and efficient strategy toward synthesis of α-haloketones from olefins under visible-light irradiation conditions was developed. In the presence of PhI(OAc)2, the reactions of styrenes with CHBr3/CHI3/CHCl3 undergo smoothly to deliver the corresponding α-bromo/iodo/chloroketones in good y...

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Bibliographic Details
Published in:Chinese chemical letters 2021-01, Vol.32 (1), p.429-432
Main Authors: Wang, Zhihui, Wang, Lei, Wang, Zhiming, Li, Pinhua, Zhang, Yicheng
Format: Article
Language:English
Subjects:
Olefins
Visible-light irradiation
α-Bromoketones
α-Chloroketones
α-Iodoketones
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Summary:A practical and efficient strategy toward synthesis of α-haloketones from olefins under visible-light irradiation conditions was developed. In the presence of PhI(OAc)2, the reactions of styrenes with CHBr3/CHI3/CHCl3 undergo smoothly to deliver the corresponding α-bromo/iodo/chloroketones in good yields under ambient conditions. [Display omitted] A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2020.02.022