Premium
Addition‐Elimination of Aryldimethylaluminum Reagents to Vinylarenes Promoted by the Addition of a Ketone
Author(s) -
Itami Kazuki,
Tanaka Shota,
Sunahara Kazuhiro,
Tatsuta Go,
Mori Atsunori
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500048
Subject(s) - chemistry , reagent , rhodium , catalysis , ketone , yield (engineering) , carbene , addition reaction , organic chemistry , cyclopentadienyl complex , medicinal chemistry , nickel , materials science , metallurgy
Addition‐elimination reactions of an arylaluminum reagent with vinylarenes is achieved mediated by a rhodium catalyst. The reaction of dimethyl(phenyl)aluminum with a rhodium(I) catalyst takes place to afford ( E )‐stilbene. The reaction is promoted by the addition of ketone as an additive to give ( E )‐stilbene in a quantitative yield. A nickel complex bearing cyclopentadienyl (Cp) and N ‐heterocyclic carbene (NHC) ligands also catalyzes the reaction to afford 1,2‐diarylethenes accompanied by a small amount of the saturated byproduct, 1,2‐diarylethanes.