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Diverse reactions of Thiophenes, Selenophenes, and Tellurophenes with strongly oxidizing I(III) PhI(L)2 Reagents

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We report the outcomes of the reactions of aromatic group 16 thiophene, selenophene, and tellurophene rings with the I(III) oxidants PhI(OAc)(OTf) and [PhI(Pyr) ][OTf] (Pyr = pyridine). In all reactions, oxidative processes take place, with generation of PhI as the reduction product. However, with the exception of tellurophene with PhI(OAc)(OTf), +4 oxidation state complexes are not observed, but rather a variety of other processes occur. In general, where a C-H unit is available on the 5-membered ring, an electrophilic aromatic substitution reaction of either −IPh or pyridine onto the ring occurs. When all positions are blocked, reactions with PhI(OAc)(OTf) give acetic and triflic anhydride as the identifiable oxidative byproducts, while [PhI(Pyr) ][OTf] gives pyridine electrophilic aromatic substitution onto the peripheral rings. Qualitative mechanistic studies indicate that the presence of the oxidizable heteroatom is required for pyridine to act as an electrophile in a substantial manner. 2 2 2 2


We thank The La Trobe Institute for Molecular Science for their generous funding of this project. This work was also supported by ARC DECRA and Future Fellowships (J.L.D., DE130100186, FT160100007).


Publication Date



Inorganic Chemistry






7p. (p. 1282-1288)


American Chemical Society



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