1192052-46-2Relevant academic research and scientific papers
Selanyl and tellanyl electrophiles as a driving force in the construction of sophisticated polyaromatic hydrocarbons
Arsenyan, Pavel,Petrenko, Alla,Belyakov, Sergey
, p. 7247 - 7255 (2021)
Herein, we report the first examples ofN-polyaromatic compounds bearing up to 13 fused aromatic rings, including 23H-benzo[12,1]tetrapheno[8,9-b]benzo[12,1]tetrapheno[9,8-h]carbazole derivatives. The reaction of selanyl and tellanyl electrophiles with ethynyl biphenyls through 6-endo-digclosure allows construction ofN-polyaromatics in a simple one-pot process under mild reaction conditions in excellent yields.
Br?nsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol-hydrocarbon biphasic system: Construction of phenanthrene frameworks
Takahashi, Ikko,Fujita, Takeshi,Shoji, Noriaki,Ichikawa, Junji
supporting information, p. 9267 - 9270 (2019/08/08)
Transition metal-free hydroarylation of unactivated alkynes was achieved by combining a Br?nsted acid catalyst and a two-phase solvent system consisting of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) and cyclohexane. This protocol is applicable to a wide variety of 2-alkynylbiaryls which leads to the synthesis of substituted phenanthrenes via 6-endo-selective ring closure. The biphasic system achieves highly efficient ring closure by appropriate separation of cationic intermediates from neutral compounds. The vinyl carbocation intermediates are stabilised in the HFIP phase, while the substrates and products are distributed in the cyclohexane phase to suppress intermolecular side reactions.
Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization
Pati, Kamalkishore,Michas, Christopher,Allenger, David,Piskun, Ilya,Coutros, Peter S.,Dos Passos Gomes, Gabriel,Alabugin, Igor V.
, p. 11706 - 11717 (2015/12/11)
The majority of Sn-mediated cyclizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an alkyne where AIBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.
Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls
Chernyak, Natalia,Gevorgyan, Vladimir
experimental part, p. 1101 - 1114 (2009/12/07)
The direct palladium-catalyzed intramolecular hydro arylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorpo
