13792-96-6Relevant articles and documents
Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds
Andicsová-Eckstein, Anita,Végh, Daniel,Kruto?íková, Al?beta,Tokárová, Zita
, p. 124 - 139 (2018)
The acid catalysed triple self-condensation of 1-thien-2-ylethanone (2-acetylthiophene) and five related compounds is presented. Tetrachlorosilane used as the Lewis acid produces dry hydrogen chloride which catalyzes the self-condensation process. Depending on the reaction conditions and the substitution of the carbonyl substrates, the reaction can proceed as a [2+2+2] cyclotrimerization towards C3-symmetric 1,3,5-trisubstituted benzenes, or as the single-type aldol condensation leading to 1,3-disubstituted (E)-β-methylchalcones. This is important for the design of new aromatic/olefinic compounds beyond the model structures. Synthesis of 4′-fluoro-3,5-di-(2-thienyl)biphenyl through a mixed-type aldol reaction using erbium triflate is discussed. Mechanistic rationale is provided.
Synthesis of C3-symmetric nano-sized polyaromatic compounds by trimerization and Suzuki-Miyaura cross-coupling reactions
Kotha, Sambasivarao,Kashinath, Dhurke,Lahiri, Kakali,Sunoj, Raghavan B.
, p. 4003 - 4013 (2007/10/03)
Various C3-symmetric molecules were prepared by trimerization of acetyl aromatic compounds and subsequently coupled with various boronic acids under Pd0 catalysis conditions to generate oligoaryl/-heteroaryl C3-symmetric molecules. Several furan- and thiophene-containing star-shaped molecules were prepared by the use of Suzuki-Miyaura cross-coupling as a key step. Structural and conformational details were explored by semi-empirical molecular orbital theory using the AM1 method. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
