Stereoselective Reduction of Alkynes: Synthesis of 4‑Organoselenyl Quinolines

• Published in: Journal of organic chemistry Vol. 87; no. 19; pp. 12710 - 12720
• Main Authors: Lutz, Guilherme, Jung, Juliano Ten Kathen, Back, Davi Fernando, Nogueira, Cristina Wayne, Zeni, Gilson
• Format: Journal Article
• Language: English
• Published: American Chemical Society 07.10.2022
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.2c01255

This study describes the reaction of 2-amino arylalkynyl ketones with organoselenolates to form (Z)-vinyl selenides, which lead to 4-organoselenyl quinolines via an intramolecular condensation. Using the optimized reaction conditions, the generality of this cyclization was studied with various arylalkynyl ketones and diorganyl diselenides. The study of the reaction mechanisms led to the isolation and identification of a vinyl selenide, which was the key intermediate for this cyclization. To expand the structural diversity and to demonstrate the applicability of the 4-organoselenyl quinolines prepared, we studied their application as substrates in the cleavage of the carbon–selenium bond using n-butyllithium followed by the capture of the lithium intermediate by electrophiles and Suzuki and Sonogashira cross-coupling reactions.