Efficient Functionalization of Organosulfones via Photoredox Catalysis: Direct Incorporation of <i>α</i>-Carbonyl Alkyl Side Chains into <i>α</i>-Allyl-<i>β</i>-Ketosulfones
Hong-Li Huang,
Shan Li,
Yong-Zheng Lv,
Ya-Qian Shi,
Tian-Tian Pang,
Ru-Fen Zhang,
Wenjing Huang,
Jianhui Yin,
Fei Gao
Affiliations
Hong-Li Huang
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Shan Li
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Yong-Zheng Lv
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Ya-Qian Shi
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Tian-Tian Pang
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Ru-Fen Zhang
College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Wenjing Huang
Institute of Translation Medicine, Shanghai University, Shanghai 200444, China
Jianhui Yin
Institute of Translation Medicine, Shanghai University, Shanghai 200444, China
Fei Gao
Institute of Translation Medicine, Shanghai University, Shanghai 200444, China
A novel and efficient method for functionalizing organosulfones has been established, utilizing a visible-light-driven intermolecular radical cascade cyclization of α-allyl-β-ketosulfones. This process employs fac-Ir(ppy)3 as the photoredox catalyst and α-carbonyl alkyl bromide as the oxidizing agent. Via this approach, the substrates experience intermolecular addition of α-carbonyl alkyl radicals to the alkene bonds, initiating a sequence of C-C bond formations that culminate in the production of organosulfone derivatives. Notably, this technique features gentle reaction conditions and an exceptional compatibility with a wide array of functional groups, making it a versatile and valuable addition to the field of organic synthesis.
