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Copper‐Catalysed Allylic Substitution Using 2,8,14,20‐Tetrapentylresorcinarenyl‐Substituted Imidazolium Salts
Author(s) -
Kaloğlu Murat,
Şahin Neslihan,
Sémeril David,
Brenner Eric,
Matt Dominique,
Özdemir İsmail,
Kaya Cemal,
Toupet Loïc
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501070
Subject(s) - chemistry , allylic rearrangement , bromide , carbene , copper , nitrogen atom , medicinal chemistry , catalysis , halide , salt (chemistry) , nitrogen , polymer chemistry , organic chemistry , group (periodic table)
Unsymmetrical imidazolium salts, each having one nitrogen atom (N1) substituted by a cavity‐shaped TPR group (TPR = 2,8,14,20‐tetrapentylresorcinaren‐5‐yl), were tested in situ as proligands for the copper‐catalysed allylic arylation of cinnamyl bromide with arylmagnesium halides. The catalytic systems produced mixtures of linear (l) and branched (b) arylated compounds in variable proportions, with the b/l ratio being the highest (78:22) for the most crowded imidazolium salt used, namely that in which the second nitrogen atom (N2) was substituted by a mesityl group. An N‐heterocyclic carbene complex obtained from one of the imidazolium salts was characterised by an X‐ray diffraction study.