Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3-Alkenes and CF3-Indanes.

Content Provider	Semantic Scholar
Author	Kazakova, Anna N. Iakovenko, Roman O. Boyarskaya, Irina A. Nenajdenko, Valentine G. Vasilyev, Aleksander V.
Copyright Year	2015
Abstract	Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH═CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar')CHCH═CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.
File Format	PDF HTM / HTML
DOI	10.1021/acs.joc.5b01398
PubMed reference number	26334780
Journal	Medline
Volume Number	80
Issue Number	19
Alternate Webpage(s)	https://dspace.spbu.ru/bitstream/11701/2038/1/untitled.pdf
Alternate Webpage(s)	https://doi.org/10.1021/acs.joc.5b01398
Journal	The Journal of organic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article