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Allenyl Thianthrenium Salt: A Bench-Stable C3 Synthon for Annulation and Cross-Coupling Reactions

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Tewari,  Srija
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University;

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Klask,  Nicolai
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute of Organic Chemistry, RWTH Aachen University;

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

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Citation

Tewari, S., Klask, N., & Ritter, T. (2024). Allenyl Thianthrenium Salt: A Bench-Stable C3 Synthon for Annulation and Cross-Coupling Reactions. Journal of the American Chemical Society, 146(40), 27282-27286. doi:10.1021/jacs.4c10135.


Cite as: https://hdl.handle.net/21.11116/0000-000F-E87F-E
Abstract
Herein, we report the first bench-stable and nonhygroscopic monosubstituted allenyl sulfonium salt (ATT) synthesized from thianthrene and propargyl alcohol. We demonstrate its use in annulation chemistry to synthesize heterocycles, such as 2-hydroxy morpholine, 2-methyl quinoxalines, and benzodioxepinone derivatives, with an exocyclic double bond. The reagent is the first allenyl sulfonium salt that can undergo palladium-catalyzed cross-coupling reactions to form a C(sp2)–C(sp2) bond via Suzuki coupling and a C(sp3)–C(sp2) bond formation via reductive coupling.