Premium
Regiodivergent Late‐Stage Pd‐ or Ru‐Catalyzed C–H Bond Functionalization Applied to the Straightforward Synthesis of N ‐Methylated Diflufenican Derivatives
Author(s) -
Benhalouche Mohamed Elhadi,
Li Haoran,
Miloudi Abdellah,
Benzai Amal,
Cordier Marie,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2020
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.202000749
Subject(s) - catalysis , regioselectivity , chemistry , palladium , bromide , surface modification , aryl , ruthenium , ring (chemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
The late‐stage C–H diversification methodology was applied to the preparation of arylated Diflufenican derivatives. Using a palladium catalyst associated with potassium pivalate, a regioselective arylation of the C–H bond flanked by the two fluorine atoms was observed. The reaction tolerated a wide range of useful functional groups on the aryl bromide. Conversely, the use of a ruthenium catalyst allowed to arylate the trifluoromethylbenzene ring of Diflufenican. To the best of our knowledge, these synthetic schemes are the first ones allowing the preparation of such arylated Diflufenican derivatives.