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Journal articles
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.
Cited literature [43 references]
https://hal-univ-rennes1.archives-ouvertes.fr/hal-02303387
Contributor : Catherine Derennes <>
Submitted on : Wednesday, April 1, 2020 - 5:19:45 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:12 PM
Contributor : Catherine Derennes <>
Submitted on : Wednesday, April 1, 2020 - 5:19:45 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:12 PM
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1860-5397-15-204.pdf
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