Strain‐Promoted 1,3‐Dithiolium‐4‐olates–Alkyne Cycloaddition

Reported here is the reactivity of mesoionic 1,3‐dithiolium‐4‐olates towards strained alkynes, leading to thiophene cycloaddition products. In the process, the potential of these dipoles towards orthogonal reaction with azides, allowing efficient double ligation reactions, was discovered. A versatil...

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Bibliographic Details
Published in:Angewandte Chemie 2019-10, Vol.131 (41), p.14686-14690
Main Authors: Kumar, Ramar Arun, Pattanayak, Manas R., Yen‐Pon, Expédite, Eliyan, Jijy, Porte, Karine, Bernard, Sabrina, Riomet, Margaux, Thuéry, Pierre, Audisio, Davide, Taran, Frédéric
Format: Article
Language:English
Subjects:
Alkynes
Chemical Sciences
Chemistry
Click-Chemie
Cycloaddition
Cycloadditionen
Dipoles
Gespannte Moleküle
Material chemistry
Organic chemistry
Synthesemethoden
Thiophene
Thiophenes
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Summary:Reported here is the reactivity of mesoionic 1,3‐dithiolium‐4‐olates towards strained alkynes, leading to thiophene cycloaddition products. In the process, the potential of these dipoles towards orthogonal reaction with azides, allowing efficient double ligation reactions, was discovered. A versatile process to access benzo[c]thiophenes, in an unprecedented divergent fashion, was developed and provides a new entry to unconventional polyaromatic thiophenes. Unter Spannung: 1,3‐Dithiolium‐4‐olate reagieren mit gespannten Alkinen, was polyaromatischen Thiophenstrukturen in hohen Ausbeuten ergibt. Ihr Nutzen für Ligationsanwendungen wurde mit Cyclooctinen untersucht, was eine neue orthogonale Reaktion zur spannungsvermittelten Azid‐Alkin‐Reaktion liefert.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201908052