1. From ferrocene to decasubstituted enantiopure ferrocene-1,1′-disulfoxide derivatives.
- Author
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Wen, Min, Erb, William, Mongin, Florence, Hurvois, Jean-Pierre, Halauko, Yury S., Ivashkevich, Oleg A., Matulis, Vadim E., Blot, Marielle, and Roisnel, Thierry
- Subjects
ENANTIOSELECTIVE catalysis ,FERROCENE ,FERROCENE derivatives ,LIGANDS (Chemistry) - Abstract
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. [ABSTRACT FROM AUTHOR]- Published
- 2023
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