Potassium hydroxide (KOH) in dimethyl sulfoxide (DMSO) forms a superbasic medium that allows one to access cross-coupling products from reactions between aryl halides with various sulfur-, oxygen-and nitrogen-based nucleophiles under transition metal-free conditions.
An efficient and clean method to construct C À C bonds has been developed via the acylation reaction of acetanilides with benzylic alcohols using tert-butyl hydroperoxide (TBHP) as oxidant catalyzed by palladium acetate in the presence of triflic acid (TfOH). The acylation reactions exhibit excellent reactivities, and up to 95% yield of the corresponding aryl ketone could be obtained under the optimal conditions.
N-and S-nucleophiles with various aryl halides proceeds smoothly in the superbasic system KOH-DMSO. This method is also applicable in intramolecular reactions to provide a transition metal-free access towards heterocyclic compounds [cf. (XII), (XIV), (XVI), (XVIII)]. -(YUAN*, Y.; THOME, I.; KIM, S. H.; CHEN, D.; BEYER, A.; BONNAMOUR, J.; ZUIDEMA, E.; CHANG, S.; BOLM, C.; Adv. Synth. Catal. 352 (2010) 17, 2892-2898, http://dx.doi.org/10.1002/adsc.201000575 ; Coll. Chem.
Palladium-Catalyzed Oxidative C-H Bond Acylation of Acetanilides with Benzylic Alcohols. -Oxidative coupling of benzylic alcohols (II) and (IV) with acetanilides (I) proceeds readily in the system tert-butyl hydroperoxide-TfOH-Pd(O-Ac)2 to afford o-aroylanilides (III) and (V), resp., in moderate to good yields. -(YUAN*, Y.; CHEN, D.; WANG, X.; Adv. Synth. Catal. 353 (2011) 18, 3373-3379, http://dx.doi.org/10.1002/adsc.201100417 ; Coll. Chem. Chem. Eng., Yangzhou Univ., Yangzhou, Jiangsu 225002, Peop. Rep. China; Eng.) -Mischke 18-041
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