From ferrocene to decasubstituted enantiopure ferrocene-1,1 '-disulfoxide derivatives
| Autor: | Min Wen, William Erb, Florence Mongin, Jean-Pierre Hurvois, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Marielle Blot, Thierry Roisnel |
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| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Belarusian State University, Agence Nationale de la Recherche (Ferrodance project), Universite de Rennes 1, CNRS, ANR-19-CE07-0015,Ferrodance,Migration d'halogène et ferrocène : une nouvelle approche vers des ferrocènes rares(2019) |
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Dalton Transactions Dalton Transactions, 2023, 52 (12), pp.3725-3737. ⟨10.1039/d2dt03456e⟩ |
| ISSN: | 1477-9226 1477-9234 |
| DOI: | 10.1039/d2dt03456e⟩ |
| Popis: | International audience; The functionalization of (R,R)-S,S '-di-tert-butylferrocene-1,1 '-disulfoxide by deprotolithiation-electrophilic trapping sequences was studied towards polysubstituted, enantiopure derivatives for which the properties were determined. While the 2,2 '-disubstituted ferrocene derivatives were obtained as expected, subsequent functionalization of the 2,2 '-di(phenylthio) and 2,2 '-bis(trimethylsilyl) derivatives occurred primarily at the 4- or 4,4 '-positions. This unusual regioselectivity was discussed in detail in light of pK(a) values and structural data. The less sterically hindered 2,2 '-difluorinated derivative yielded the expected 1,1 ',2,2 ',3,3 '-hexasubstituted ferrocenes by the deprotometallation-trapping sequence. Further functionalization proved possible, leading to early examples of 1,1 ',2,2 ',3,3 ',4,4 '-octa, nona and even decasubstituted ferrocenes. Some of the newly prepared ferrocene-1,1 '-disulfoxides were tested as ligands for enantioselective catalysis and their electrochemical properties were investigated. |
| Databáze: | OpenAIRE |
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