Journal
MOLECULES
Volume 27, Issue 6, Pages -Publisher
MDPI
DOI: 10.3390/molecules27061798
Keywords
ferrocene; sulfoxide; deprotonative metalation; chiral directing group; CH acidity; stereoselectivity; one-pot synthesis
Funding
- Agence Nationale de la Recherche (Ferrodance project)
- Universite de Rennes 1
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The study aimed to design synthetic methodologies for the synthesis of polysubstituted ferrocenesulfoxides using polar organometallic reagents. By introducing a third substituent and removing specific groups, enantiopure ferrocenesulfoxides with various substitution patterns were successfully synthesized.
The purpose of the study is to design synthetic methodologies, especially directed deprotometalation using polar organometallic reagents, to access polysubstituted ferrocenesulfoxides. From enantiopure 2-substituted (SiMe3, PPh2) S-tert-butylferrocenesulfoxides, a third substituent was first introduced at the 5 position (SiMe3, I, D, C(OH)Ph-2, Me, PPh2, CH2NMe2, F) and removal of the trimethylsilyl group then afforded 2-substituted ferrocenesulfoxides unreachable otherwise. Attempts to apply the halogen dance reaction to the ferrocenesulfoxide series led to unexpected results although rationalized in light of calculated pK(a) values. Further functionalizations were also possible. Thus, new enantiopure, planar chiral di- and trisubstituted ferrocenes have been obtained, in addition to several original 2-substituted, 2,3- and 2,5-disubstituted, 2,3,5-trisubstituted and even 2,3,4,5-tetrasubstituted ferrocenesulfoxides, also enantiopure.
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