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

Publication date: Available online 14 February 2020Source: Chinese Chemical LettersAuthor(s): Zhihui Wang, Lei Wang, Zhiming Wang, Pinhua Li, Yicheng ZhangAbstractA 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-bromoketonesand α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED(450−455 nm) irradiation.Graphical AbstractA 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.

Source: Chinese Chemical Letters - February 14, 2020 Category: Chemistry Source Type: research