α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation

Jia, Hao; Ritter, Tobias

doi:10.1002/anie.202208978

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α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation

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Jia, Hao
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter, Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Jia, H., & Ritter, T. (2022). α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation. Angewandte Chemie International Edition, 61(39): e202208978. doi:10.1002/anie.202208978.

Cite as: https://hdl.handle.net/21.11116/0000-000B-1B53-A

Abstract

Here we report an α-thianthrenium carbonyl species, as the equivalent of an α-carbonyl carbocation, which is generated by the radical conjugate addition of a trifluoromethyl thianthrenium salt to Michael acceptors. The reactivity allows for the synthesis of C^α-tetrasubstituted α- and β-amino acid analogues via a Ritter reaction by addition of acetonitrile. Addition of hydroxide, methoxide, and even fluoride can afford α-heteroatom substituted α-phenylpropanoates.