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Article Dans Une Revue Molecules Année : 2022

Synthesis of Polysubstituted Ferrocenesulfoxides

Résumé

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 (SiMe, PPh) --butylferrocenesulfoxides, a third substituent was first introduced at the 5 position (SiMe, I, D, C(OH)Ph, Me, PPh, CHNMe, 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 p 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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hal-03632094 , version 1 (06-04-2022)

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Min Wen, William Erb, Florence Mongin, Yury S Halauko, Oleg A Ivashkevich, et al.. Synthesis of Polysubstituted Ferrocenesulfoxides. Molecules, 2022, 27 (6), pp.1798. ⟨10.3390/molecules27061798⟩. ⟨hal-03632094⟩
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