1. Electrophilic Stannylation of Arenes: A New SEAr Reaction
- Author
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Vladimir V. Grushin, David L. Thorn, and William J. Marshall
- Subjects
chemistry.chemical_element ,General Chemistry ,Electrophilic aromatic substitution ,Tin oxide ,chemistry.chemical_compound ,chemistry ,Main group element ,Electrophile ,Polymer chemistry ,Trifluoroacetic acid ,Organic chemistry ,Trifluoroacetic anhydride ,Tin ,Benzene - 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.
- Published
- 2001
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