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Regioselective Pd-catalyzed direct C1-and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

Abstract : The Pd-catalyzed C-H bond functionalization of lilolidine was investigated. The use of a palladium-diphosphine catalyst associated to acetate bases in DMA was found to promote the regioselective arylation at alpha-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these alpha-arylated lilolidines, a second arylation at the beta-position gives the access to alpha,beta-diarylated lilolidines containing two different aryl groups. The one pot access to alpha,beta-diarylated lilolidines with two identical aryl groups is also possible by using a larger amount of aryl bromide. The synthesis of 5,6-dihydrodibenzo[a,c]pyrido[3,2,1-jk]carbazoles from lilolidine via three successive direct arylations is also described. Therefore, this methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C-H bond functionalization steps allowing to tune their biological properties.
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Hai-Yun Huang, Haoran Li, Thierry Roisnel, Jean-François Soulé, Henri Doucet. Regioselective Pd-catalyzed direct C1-and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives. Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2019, 15, pp.2069-2075. ⟨10.3762/bjoc.15.204⟩. ⟨hal-02303387⟩

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