Abstract
The application of ethynylferrocene, FcC≡CH (1), as a highly efficient electroactive precursor for the thiol–yne click reaction is presented. For this purpose, a wide range of functionalized thiols, namely 2-mercaptoethanol, 1-thioglycerol, 3-mercaptopropionic acid, 4-aminothiophenol, and benzene-1,3-dithiol as well as tetrathiol pentaerythritol tetrakis(3-mercaptopropionate), were investigated. This facile thiol–ethynylferrocene radical reaction has resulted in the quantitative formation and isolation of the newly ferrocenyl–vinyl sulfides FcCH═CHS(CH2)2OH (2Z and 2E), FcCH═CHSCH2CH(OH)CH2OH (3Z and 3E), FcCH═CHS(CH2)2COOH (4Z and 4E), FcC(CH2)S(1,4-C6H4)NH2 (5α), FcCH═CHS(1,3-C6H4)SCH═CHFc (6), and [FcCH═CHS(CH2)2COOCH2]4C (7). Thiol–ethynylferrocene reactions have been initiated either by heat, in toluene with AIBN, or by UV light irradiation in THF in the presence of DMPA as photoinitiator. The outcome of the hydrothiolation of ethynylferrocene strongly depends on the thiol structure and on the initia...
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