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Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones |
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| Authors: | Stefan Jopp Tina Wallaschkowski Peter Ehlers Eva Frank Gyula Schneider János Wölfling Erzsébet Mernyák Alexander Villinger Peter Langer |
| Affiliation: | 1. University of Rostock, Institute of Chemistry, Albert-Einstein-Str. 3a, 18059, Rostock, Germany;2. Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, 18059, Rostock, Germany;3. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720, Szeged, Hungary |
| Abstract: | 4-Bromo-3-O-triflyl-estrone has been synthesized in 2 steps from estrone and was successfully employed in chemoselective palladium catalysed Suzuki-Miyaura reactions. Mono- and bis-arylations were carried out selectively by variation of ligands and solvents. Overall 19 derivatives of mono- and bis-arylated estrones were synthesized under optimized conditions in high yields. Various products showed atropisomerism which was studied in detail by NMR spectroscopy. |
| Keywords: | Steroids Cross-coupling reactions Palladium Chemoselectivity Palladium |
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