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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000F-E87F-E Version Permalink: https://hdl.handle.net/21.11116/0000-000F-EFFF-6
Genre: Journal Article

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 Creators:
Tewari, Srija1, 2, Author           
Klask, Nicolai1, 2, Author           
Ritter, Tobias1, Author           
Affiliations:
1Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              
2Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, ou_persistent22              

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 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.

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Language(s): eng - English
 Dates: 2024-07-252024-09-242024-10-09
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.4c10135
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 146 (40) Sequence Number: - Start / End Page: 27282 - 27286 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870