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Environmentally‐Safe Conditions for a Palladium‐Catalyzed Direct C3‐Arylation with High Turn Over Frequency of Imidazo[1,2‐ b ]pyridazines Using Aryl Bromides and Chlorides
Author(s) -
Chikhi Sabah,
Djebbar Safia,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600827
Subject(s) - catalysis , pyridazine , aryl , chemistry , palladium , phosphine , medicinal chemistry , ether , organic chemistry , combinatorial chemistry , alkyl
Pd(OAc) 2 was found to catalyze very efficiently the direct arylation of imidazo[1,2‐ b ]pyridazine at C3‐position under a very low catalyst loading and phosphine‐free conditions. The reaction can be performed in very high TOFs and TONs employing as little as 0.1–0.05 mol % catalyst using a wide range of aryl bromides. In addition, some electron‐deficient aryl chlorides were also found to be suitable substrates. Moreover, 31 examples of the cross couplings were reported using green, safe, and renewable solvents, such as pentan‐1‐ol, diethylcarbonate or cyclopentyl methyl ether, without loss of efficiency.