Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

Nikolay V Lukashev; Gennadii A Grabovyi; Dmitry A Erzunov; Alexey V Kazantsev; Gennadij V Latyshev; Alexei D Averin; Irina P Beletskaya

doi:10.3762/bjoc.13.55

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

Beilstein J Org Chem. 2017 Mar 20:13:564-570. doi: 10.3762/bjoc.13.55. eCollection 2017.

Authors

Nikolay V Lukashev¹, Gennadii A Grabovyi¹, Dmitry A Erzunov¹, Alexey V Kazantsev¹, Gennadij V Latyshev¹, Alexei D Averin¹, Irina P Beletskaya¹

Affiliation

¹ Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russia.

Abstract

Cu- and Pd-catalyzed arylation of aminocholanes has been described for the first time. While this Cu-catalyzed protocol provides high yields in reactions of aminocholanes with iodoarenes, Pd catalysis was found to be preferable for the reactions of aminocholanes with dichloroanthraquinones. UV-vis titration of bis(cholanylamino)anthraquinones with a series of cations demonstrated their high binding affinity to Cu²⁺, Al³⁺, and Cr³⁺.

Keywords: Cu-catalysis; Pd-catalysis; amination; aminocholanes; bile acids; cation complexation; diaminoanthraquinone.