Strain-Promoted 1,3-Dithiolium-4-olates-Alkyne Cycloaddition.

Authors :: Kumar RA
Pattanayak MR
Yen-Pon E
Eliyan J
Porte K
Bernard S
Riomet M
Thuéry P
Audisio D
Taran F
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Oct 07; Vol. 58 (41), pp. 14544-14548. Date of Electronic Publication: 2019 Sep 04.
Publication Year :: 2019
Abstract: 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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)