2005
DOI: 10.1021/ol0523143
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A Convenient FeCl3-Catalyzed Hydroarylation of Styrenes

Abstract: [reaction: see text] 1,1-Diarylalkanes are easily synthesized by CH-functionalization reactions of electron-rich arenes and heteroarenes with styrenes in the presence of FeCl(3) as catalyst.

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Cited by 216 publications
(92 citation statements)
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“…Furthermore, by variation of the electrophilic reagent a 100 %-atom efficient addition of aromatic olefins to arenes was realized. [2] Based on this work, we became interested in the direct benzylation of 1,3-dicarbonyl compounds with 1-phenylethanol. The resulting structural motif is found in a number of biologically active compounds (Scheme 1).…”
mentioning
confidence: 99%
“…Furthermore, by variation of the electrophilic reagent a 100 %-atom efficient addition of aromatic olefins to arenes was realized. [2] Based on this work, we became interested in the direct benzylation of 1,3-dicarbonyl compounds with 1-phenylethanol. The resulting structural motif is found in a number of biologically active compounds (Scheme 1).…”
mentioning
confidence: 99%
“…26 While this chemistry was recently extended to include the intermolecular hydroarylation of styrenes and simple R-olefins with 1,2-disubstituted indoles, 27 it requires high temperatures and exhibits e2:1 selectivity for the Markovnikov product when styryl olefins are used. Friedel-Crafts-type hydroarylations of styrenes with anisole, thiophene, and xylene nucleophiles under Lewis acid catalysis have also been recently reported, [28][29][30] but require the use of superstoichiometric arene (g4 equiv) and have not been extended to indole nucleophiles.…”
Section: Selection For Bond Formation In Organic Solvents and At Highmentioning
confidence: 99%
“…4,5 Most of these reactions have some drawbacks such as the need for severe reaction conditions (high temperature, strong acidic conditions), low selectivity, moisture sensitivity, high cost, and large amounts of waste materials. 6 Therefore, great efforts have been devoted to search for the more mild reaction conditions such as low temperature, short reaction time, small amounts of catalyst, etc.…”
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confidence: 99%