Electrophilic stannylation of arenes: A new SEAr reaction

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...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 343; no. 5; pp. 433 - 438
Main Authors Grushin, VV, Marshall, WJ, Thorn, DL
Format Journal Article
LanguageEnglish
Published BERLIN Wiley 01.07.2001
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
C-H activation
arenes
CRYSTAL-STRUCTURE
stannylation
COMPLEXES
tin
aromatic substitution
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Summary: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)(2)Sn4O2(CF3COO)(10) and (xylyl)(2)Sn4O2(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 trifluoroacelato complexes can metalate arenes by C-H activation.
ISSN:1615-4150
DOI:10.1002/1615-4169(200107)343:5<433::AID-ADSC433>3.3.CO;2-V