A Radical
Smiles Rearrangement Promoted by Neutral
Eosin Y as a Direct Hydrogen Atom Transfer Photocatalyst
Posted on 2020-06-22 - 22:04
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.
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Yan, Jianming; Cheo, Han Wen; Teo, Wei Kiat; Shi, Xiangcheng; Wu, Hui; Idres, Shabana Binte; et al. (2020). A Radical
Smiles Rearrangement Promoted by Neutral
Eosin Y as a Direct Hydrogen Atom Transfer Photocatalyst. ACS Publications. Collection. https://doi.org/10.1021/jacs.0c02052