68498-64-6Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of pyrrole anions with aryl chlorides, bromides, and iodides
Rieth, Ryan D.,Mankad, Neal P.,Calimano, Elisa,Sadighi, Joseph P.
, p. 3981 - 3983 (2007/10/03)
(Chemical Equation Presented) A general method for the conversion of pyrrole anions to 2-arylpyrroles has been developed. Using a palladium precatalyst and sterically demanding 2-(dialkylphosphino)biphenyl ligands, (pyrrolyl)zinc chloride may be cross-coupled with a wide range of aryl halides, including aryl chlorides and aryl bromides, at low catalyst loadings and under mild conditions. A high degree of steric hindrance is tolerated. Certain ring-substituted pyrrole anions have also been arylated with aryl bromide substrates.
Easy photochemical preparation of 2-dimethylaminophenylfurans, -pyrroles and -thiophenes
Guizzardi, Benedetta,Mella, Mariella,Fagnoni, Maurizio,Albini, Angelo
, p. 9383 - 9389 (2007/10/03)
2-(4-N,N-dimethylaminophenyl) heterocycles are smoothly obtained from the photolysis of 4-chloro-N,N-dimethylaniline in acetonitrile in the presence of furan, pyrrole, thiophene and some of their methyl derivatives bearing a free α-position. With 2,5-dimethyl heterocycles the arylation occurs with equal efficiency in the β position. In the case of furan, when the irradiation is carried out in methanol, cis/trans 2-aryl-5-methoxy-2,5-dihydro adducts are obtained. The reaction is rationalized as involving heterolytic cleavage of the C-Cl bond in the triplet state of the aniline. The intermediacy of the thus formed triplet aryl cation explains the observed high regio- and chemo-selectivity of the process. (C) 2000 Elsevier Science Ltd.
