An Unexpected C–C Bond Cleavage of Acetophenones: Synthesis of Bis(heteroaryl)arylmethanes and Triarylmethanes via SeO2/Lanthanide Chloride Catalyzed Friedel–Crafts Arylation

Abstract A novel synthesis of bisheteroarylaryl methanes and triarylmethanes is described by the selective C–C bond cleavage of acetophenones in the presence of SeO 2 /lanthanide chlorides. The present strategy provides an in situ generation of aldehydes from acetophenones followed by a double Fried...

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Bibliographic Details
Published in:Synlett 2016-03, Vol.27 (4), p.631-639
Main Authors: Kumar, G. Santosh, Kumar, A. Sanjeeva, Swetha, A., Babu, B. Madhu, Meshram, H. M.
Format: Article
Language:English
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Summary:Abstract A novel synthesis of bisheteroarylaryl methanes and triarylmethanes is described by the selective C–C bond cleavage of acetophenones in the presence of SeO 2 /lanthanide chlorides. The present strategy provides an in situ generation of aldehydes from acetophenones followed by a double Friedel–Crafts reaction of electron-rich arenes. Natural product 1,1,1-tris(3-indolyl)methane is synthesized in a single step following the same protocol.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0035-1560808