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Reactivity of 4‐phenylthiazoles in ruthenium catalyzed direct arylations
Author(s) -
Daher Ahmad,
Jacquemin Denis,
Guerchais Véronique,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2019
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.4794
Subject(s) - chemistry , reactivity (psychology) , ruthenium , aryl , substituent , catalysis , medicinal chemistry , catalytic cycle , base (topology) , combinatorial chemistry , organic chemistry , alkyl , medicine , mathematical analysis , alternative medicine , mathematics , pathology
The reactivity of the phenyl substituent of 4‐phenylthiazoles in Ru‐catalyzed direct arylation was studied. 4‐Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5‐position of 4‐phenylthiazole enhances its reactivity, allowing the selective mono‐arylation of the phenyl unit of 4‐phenylthiazoles in moderate to high yields using 5 mol% of [Ru( p ‐cymene)Cl 2 ] 2 catalyst precursor associated to KOPiv as base. These results reveal that the conformation and electronic properties of 4‐phenylthiazoles are crucial to allow the formation of suitable intermediates in the course of the catalytic cycle. The reaction tolerated both electron‐rich and electron‐poor aryl bromides allowing the straightforward tuning of the electronic properties of the arylated 2‐methyl‐4‐phenyl‐5‐arylthiazoles.