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DOI: 10.1055/a-2609-2989
In Situ Generated Phenothiazine Sulfoxide Enables Reductive γ-Lactone Synthesis via Peroxide Activation
Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones.
J. Am. Chem. Soc. 2025;
147: 12908-12916
DOI: 10.1021/jacs.5c01988
Significance
Glorius, Wenger and co-workers introduce N-phenylphenothiazine sulfoxide (PTH-O) as a highly efficient photocatalyst for the synthesis of γ-lactones from cyclic malonyl peroxides and styrene derivatives. The active catalyst species, generated in situ from a simple precursor, enables the single-electron reduction of cyclic malonyl peroxides, initiating a sequence leading to γ-lactone formation. The approach demonstrates broad substrate scope and good functional group tolerance.
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Comment
A comprehensive mechanistic study reveals a distinct catalytic cycle involving an oxidized phenothiazine derivative. Although phenothiazines are well-established for their strong reducing capabilities, their oxidized forms had been largely overlooked. This work highlights previously unrecognized reactivity and provides valuable insights for the strategic development of more efficient and selective catalytic systems.
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Publication History
Article published online:
23 June 2025
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