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Strain‐Promoted 1,3‐Dithiolium‐4‐olates–Alkyne Cycloaddition
Author(s) -
Kumar Ramar Arun,
Pattanayak Manas R.,
YenPon Expédite,
Eliyan Jijy,
Porte Karine,
Bernard Sabrina,
Riomet Margaux,
Thuéry Pierre,
Audisio Davide,
Taran Frédéric
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201908052
Subject(s) - cycloaddition , mesoionic , chemistry , reactivity (psychology) , alkyne , thiophene , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology
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.