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A Radical Smiles Rearrangement Promoted by Neutral Eosin Y as a Direct Hydrogen Atom Transfer Photocatalyst

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posted on 22.06.2020, 22:04 by Jianming Yan, Han Wen Cheo, Wei Kiat Teo, Xiangcheng Shi, Hui Wu, Shabana Binte Idres, Lih-Wen Deng, Jie Wu
A visible-light-mediated radical Smiles rearrangement has been achieved using neutral eosin Y as a direct hydrogen atom transfer (HAT) photocatalyst. Novel N-heterocycles as single diastereomers featuring an isothiazolidin-3-one 1,1-dioxide moiety are directly accessed by this method. A wide range of functional groups can be incorporated in the products by employing diverse aldehydes and N-(hetero)­arylsulfonyl propiolamides. The transformation proceeds through a cascade of visible-light-induced HAT, 1,4-addition, Smiles rearrangement, 5-endo-trig cyclization, and a reverse HAT process. Preliminary biological studies of the highly functionalized heterocyclic compounds suggest potential anticancer activity with some of the synthesized compounds.