Beilstein J. Org. Chem.2019,15, 2069–2075, doi:10.3762/bjoc.15.204
Hai-Yun Huang Haoran Li Thierry Roisnel Jean-Francois Soule Henri Doucet Univ Rennes, CNRS, ISCR-UMR 6226, F-35000 Rennes, France 10.3762/bjoc.15.204 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 α-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these α-arylated lilolidines, a second arylation at the β-position gives the access to α,β-diarylated lilolidines containing two different aryl
groups. The one pot access to α,β-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
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Graphical Abstract
Figure 1:
Structures of lilolidine, tivantinib and tarazepide.