The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

Beilstein Journal of Organic Chemistry

卷:14

Lilla Fekete¹  Dávid Szemerédi²  Gyula Schneider²  Ildikó Bacsa²  Erzsébet Mernyák²  János Wölfling² 

[1] Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;

[2] Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;

关键词: aminoestrones;    Buchwald–Hartwig amination;    13α-estrone;    functionalization;    microwave assisted reactions;   

DOI  :  10.3762/bjoc.14.85

来源: DOAJ

【 摘 要 】

A facile Pd-catalyzed C(sp2)–N coupling to provide a range of 2- or 4-[(subst.)phenyl]amino-13α-estrone derivatives has been achieved under microwave irradiation. The reactions were mediated with the use of Pd(OAc)2 as a catalyst and KOt-Bu as a base in the presence of X-Phos as a ligand. The desired products have been obtained in good to excellent yields. The nature and the position of the aniline substituent at the aromatic ring influenced the outcome of the couplings. 2-Amino-13α-estrone was also synthesized in a two-step protocol including an amination of 2-bromo-13α-estrone 3-benzyl ether with benzophenone imine and subsequent hydrogenolysis.

【 授权许可】

Unknown