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In situ generation of highly active bis(N‐heterocyclic)carbene palladium as an efficient catalyst in direct S ‐arylation of methylphenyl sulfoxide and the Heck reaction: Ligand steric effects in product selectivity
Author(s) -
Bagherzadeh Mojtaba,
Mousavi Nargesalsadat,
Jamali Sirous
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3677
Subject(s) - chemistry , carbene , sulfoxide , aryl , heck reaction , palladium , alkyl , isopropyl , catalysis , ligand (biochemistry) , denticity , medicinal chemistry , steric effects , organic chemistry , combinatorial chemistry , crystal structure , biochemistry , receptor
The use of 1,3‐bis(N‐heterocyclic)carbene ligands with different alkyl wingtip groups (alkyl = methyl, isopropyl and tert ‐butyl) is an effective method for the palladium‐catalysed direct S ‐arylation of methylphenyl sulfoxide and C–C coupling of various of aryl halides with alkenes. The reactions proceed in moderate to good yields. Interestingly, it is shown experimentally that, by using bulkier bidentate N‐heterocyclic carbene ligands, more selective catalytic systems towards cis products in Heck coupling reactions can be achieved.