64150-61-4Relevant articles and documents
Aromatic and Antiaromatic Pathways in Triphyrin(2.1.1) Annelated with Benzo[b]heterocycles
Bartkowski, Krzysztof,Dimitrova, Maria,Chmielewski, Piotr J.,Sundholm, Dage,Pawlicki, Mi?osz
, p. 15477 - 15482 (2019)
Understanding of the aromatic properties and magnetically induced current densities of highly conjugated chromophores is important when designing molecules with strongly delocalized electronic structure. Linear extension of the triphyrin(2.1.1) skeleton with an annelated benzo[b]heterocycle fragment modifies the aromatic character by extending the electron delocalization pathway. Two-electron reduction leads to an antiaromatic triphyrin(2.1.1) ring and an aromatic benzo[b]heterocycle subunit. Current-density calculations provide detailed information about the observed pathways and their strengths.
Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis
Rao, Maddali L. N.,Talode, Jalindar B.,Murty, Venneti N.
supporting information, p. 2065 - 2076 (2016/10/05)
A regio- and chemoselective cross-coupling study using 2,3-dibromobenzofurans and 2,3,5-tribromobenzofuran was achieved with sub-stoichiometric loadings of triarylbismuths as atom-economic reagents under Pd-catalyzed conditions. As part of this study, various 2,3-diaryl- and 2,3,5-triarylbenzofuran products were obtained in high yields, involving one-pot operations and short reaction times.
Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study
Ali Salman, Ghazwan,Un Nisa, Riffat,Iaroshenko, Viktor O.,Iqbal, Jamshed,Ayub, Khurshid,Langer, Peter
, p. 9464 - 9473 (2013/01/15)
Benzofuroquinolines were prepared by a new type of Pd catalyzed annulation reaction. In the first step, 2-alkynyl-3-bromobenzofurans were prepared by Sonogashira reactions of 2,3-dibromobenzofuran. Their Pd catalyzed reaction with electron-rich anilines afforded benzofuroquinolines by a domino C-N coupling/annulation process. This reaction proceeds as a C,N-cyclization via the nitrogen atom and the ortho-carbon of the aniline. Similarly, furoquinolines were prepared from 2,3-dibromofuran. In contrast, benzofuropyrroles and furopyrroles were formed by N,N-cyclization when electron-poor anilines were used. Earlier, we reported results related to the thiophene and benzothiophene series. Quinolines were formed from 2,3-dibromobenzothiophene when electron rich anilines were used. In contrast, pyrroles were obtained in the case of electron-poor anilines. On the other hand, pyrroles were generally obtained, not depending on the type of aniline, when 2,3-dibromothiophene was employed as the starting material. In the present article, a detailed DFT study related to the mechanism (quinoline versus pyrrole formation) is reported which provides a rationalization of the selectivities observed for the furan, benzofuran, thiophene and benzothiophene series and for the different selectivities observed for electron-rich and -poor anilines.