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Paper | Special issue | Vol 99, No. 1, 2019, pp.301-309
Published online, 19th October, 2018
DOI: 10.3987/COM-18-S(F)24
Four-Component Coupling Strategy for 2,3,4-Trisubstituted 3,4-Dihydroquinoline

Hiroki Yamagishi, Shun Tsuchiya, Hayate Saito, Keisuke Nogi, Jun Shimokawa, and Hideki Yorimitsu*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan


Trimethylsilyllithium attacked selectively at the 4-position of 2-(methylsulfanyl)quinoline. The lithium enamide intermediate generated in situ reacted with a series of electrophiles to introduce a substituent at the 3-position of the dihydroquinoline skeleton. Combined with the conversion of the 2-methylsulfanyl group to an aryl group via palladium-catalyzed Negishi-type coupling reaction, the net four-component coupling transformation in two steps provided a 2,3,4-trisubstituted 3,4-dihydroquinoline skeleton.