RSS-Feed abonnieren
DOI: 10.1055/a-2348-7588
Ru-mediated and sulfur-directed ortho-C-H activation of benzyl thioethers with internal alkynes and selective hydro-thiolation of acetylene dicarboxylates
Gefördert durch: Council of Scientific and Industrial Research, India CSIR (01(2996)/19/EMR-II)![](https://www.thieme-connect.de/media/synthesis/0000AAM/lookinside/thumbnails/10.1055-a-2348-7588-1.jpg)
In this report, we have established a Ru(η6-C6H6)Cl2 catalyzed ortho-C-H activation of benzylthioethers with alkynes under milder reaction conditions. The sulfur atom of benzyl thioethers worked as directing group for ortho-C-H activation of benzylthioethers. The reaction was found to be well tolerated towards a range of benzylthioethers as well as alkynes. Moreover, the reaction is significantly influenced by the length of alkyl and aryl thioether, while the best results were obtained with benzyl thioethers. Kinetic isotopic experiments suggest that the ortho-C-H bond breaking is not a rate-determining step for present reaction. Apart from ortho-CH activation, under the same reaction conditions, a selective debenzylative hydro-thiolation was exclusively obtained with acrylates, which broadens the synthetic impact of benzylthioethers for the preparation of mixed chalcogen ethers. Moreover, it is an unusual observation and not yet reported.
Publikationsverlauf
Eingereicht: 11. April 2024
Angenommen nach Revision: 19. Juni 2024
Accepted Manuscript online:
19. Juni 2024
© . Thieme. All rights reserved.
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany