In(OTf)3-Catalyzed Highly Chemo- and Regioselective Head-to-Tail Heterodimerization of Vinylarenes with 1,1-Diarylethenes

In(OTf)3-Catalyzed Highly Chemo- and Regioselective Head-to-Tail Heterodimerization of Vinylarenes with 1,1-Diarylethenes

Cross combination: The olefinic CH bond in 1,1‐diarylethenes selectively adds to the CC double bond of substituted styrenes in a head‐to‐tail fashion under In(OTf)3 (OTf=triflate) catalysis (see scheme) while homo‐ and cyclodimerization reactions are suppressed. The high chemo‐ and regioselectivit...

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Veröffentlicht in:Chemistry : a European journal 2011-07, Vol.17 (30), p.8290-8293
Hauptverfasser: Dai, Jing, Wu, Jinlong, Zhao, Guanglian, Dai, Wei-Min
Format: Artikel
Sprache:eng
Schlagworte:
alkenes
carbocations
Chemistry
CH activation
hydroalkenylation
Lewis acids
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Zusammenfassung:Cross combination: The olefinic CH bond in 1,1‐diarylethenes selectively adds to the CC double bond of substituted styrenes in a head‐to‐tail fashion under In(OTf)3 (OTf=triflate) catalysis (see scheme) while homo‐ and cyclodimerization reactions are suppressed. The high chemo‐ and regioselectivity of this intermolecular hydroalkenylation originates from the high stability and steric bulk of the diaryl‐substituted tertiary carbocation intermediate.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201101190