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 International Edition 2019-10, Vol.58 (41), p.14544-14548
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
click chemistry
Cycloaddition
Dipoles
strained molecules
synthetic methods
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. Under strain: 1,3‐dithiolium‐4‐olates reacted with strained alkynes, affording polyaromatic thiophene structures in high yields. Their use for ligation applications has also been investigated with cyclooctynes, offering a new orthogonal reaction to the strain‐promoted azide–alkyne reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201908052