Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
AlCl3-mediated Defluorinative Diarylhydroxylation Transformation of CF3: Chemoselective Arylation of CF3 and Chlorocarbonyl Groups Attached to Aromatic Rings
Akiko OkamotoKazuhiro KumedaNoriyuki Yonezawa
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2010 Volume 39 Issue 2 Pages 124-125

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Abstract

The CF3 group in 4-trifluoromethylbenzoyl chloride is efficiently diarylated and converted into a diarylhydroxymethyl group by treatment with AlCl3 in the presence of an excess amount of halobenzene (C6H5X; X = F, Cl, and Br). The diarylation is followed by arylation of the chlorocarbonyl group to afford triarylated products, diarylhydroxymethylated benzophenones. The employment of TfOH in place of AlCl3 promotes the exclusive arylation of the chlorocarbonyl group leaving the CF3 group unchanged to afford selectively 4-trifluoromethylbenzophenones, which then undergo diarylhydroxymethylation with the aid of AlCl3.

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© 2010 The Chemical Society of Japan
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