75251-27-3Relevant articles and documents
Palladium-Catalyzed Mono-α-arylation of Acetone at Room Temperature
Macqueen, Preston M.,Chisholm, Alicia J.,Hargreaves, Breanna K. V.,Stradiotto, Mark
, p. 11006 - 11009 (2015)
The first examples of acetone mono-α-arylation at room temperature are described, enabled by use of a [Pd(cinnamyl)Cl]2/JosiPhos catalyst system. (Hetero)aryl chloride, bromide, and iodide electrophiles featuring or lacking ortho-substitution, and comprising a range of functionalities (e.g., alkoxy, cyano, fluoro, trifluoromethyl, or alkenyl) and heteroaryl motifs (e.g., pyrrole, pyridine, isoquinoline, quinoline, quinaldine, (benzo)thiophene, benzothiazole, or benzodioxole) were successfully accommodated. Proof-of-principle experiments confirm that other (hetero)aryl methyl ketones can also be employed in such room temperature mono-α-arylations. The established substrate scope is the most extensive reported to date for acetone mono-α-arylation under any conditions, and more generally represents the first room temperature ketone mono-α-arylations employing a structurally diverse set of (hetero)aryl chlorides. Chill out: The first examples of acetone mono-α-arylation at room temperature are described. The substrate scope is the most extensive reported to date for acetone mono-α-arylation under any conditions, and represents the first room temperature ketone mono-α-arylations employing a diverse set of (hetero)aryl chlorides.
New Rearrangements of Arylhydrazones in Polyphosphoric Acid: Extension to the Thiophene and Indole Series. 5
Fusco, Raffaello,Sannicolo, Franco
, p. 1691 - 1696 (2007/10/02)
The behavior toward polyphosphoric acid of arylhydrazones of a few heterocyclic carbonyl compounds of the thiophene and indole series is described.The phenylhydrazone and 2,6-dimethylphenylhydrazone of ethyl α-thienylglyoxylate gave ethyl 4- and 5-(4-aminoaryl)-α-thienylglyoxylate, arising from two different sigmatropic rearrangements.The N,3,5-trimethylphenylhydrazone of 2-methylindole-3-carboxaldehyde afforded the 4--2-methylindole-3-carboxaldehyde resulting from a sigmatropic rearrangement, while the 2,6-dimethylphenylhydrazone of the same carbonyl compound unexpectedly gave the 3-(4-amino-3,5-dimethylphenyl)-2-methylindole-3-carboxaldehyde generated through a sigmatropic reaction.Chemical evidences are given for the assigned structures.
