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

Hai-Yun Huang 1 Haoran Li 1 Thierry Roisnel 1 Jean-François Soulé 1 Henri Doucet 1
1 ISCR - Institut des Sciences Chimiques de Rennes
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.
Keywords : catalysis C-C bond formation C-H bond activation lilolidine palladium
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Journal articles
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-02303387
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, October 2, 2019 - 11:51:29 AM
Last modification on : Thursday, October 3, 2019 - 1:22:44 AM

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UNIV-RENNES1 | ISCR | SCR-CD | CNRS | UR1-UFR-SPM | INC-CNRS | UNIV-RENNES | INSA-GROUPE

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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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