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Electrophilic Stannylation of Arenes: A New SEAr Reaction
Authors:Vladimir V Grushin  William J Marshall  David L Thorn
Abstract:Electrophilic “trifluoroacetatotin(IV)” has been prepared by reaction of tin oxide with trifluoroperacetic acid/trifluoroacetic anhydride, and by reaction of tetraphenyltin with excess trifluoroacetic acid. The electrophilic tin(IV) material prepared by either route reacts reversibly with arenes to make aryl‐tin compounds and trifluoroacetic acid. The compounds (C6H5)2Sn4O2(CF3COO)10 and (xylyl)2Sn4O2(CF3COO)10 have been obtained from the reactions with benzene and p‐xylene, respectively, and their molecular structures determined by X‐ray crystallography. Tin now joins Pb, Tl, and Hg in the list of main group metals whose trifluoroacetato complexes can metalate arenes by C−H activation.
Keywords:arenes  aromatic substitution  C‐H activation  stannylation  tin
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