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In(OTf) 3 ‐Catalyzed Highly Chemo‐ and Regioselective Head‐to‐Tail Heterodimerization of Vinylarenes with 1,1‐Diarylethenes
Author(s) -
Dai Jing,
Wu Jinlong,
Zhao Guanglian,
Dai WeiMin
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101190
Subject(s) - regioselectivity , carbocation , steric effects , intermolecular force , chemistry , double bond , trifluoromethanesulfonate , catalysis , stereochemistry , photochemistry , organic chemistry , molecule
Cross combination : The olefinic CH bond in 1,1‐diarylethenes selectively adds to the CC 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.