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Article Dans Une Revue Organic Letters Année : 2016

Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through Three Palladium-Catalyzed C-H Bond Arylations

W. Hagui
  • Fonction : Auteur
N. Besbes
  • Fonction : Auteur
E. Srasra
  • Fonction : Auteur
T. Roisnel

Résumé

An expeditious synthesis of a wide range of phenanthro[9,10-b]thiophene derivatives, which are a class of polyaromatic hydrocarbon (PAH) containing a sulfur atom, is reported. The synthetic scheme involves only two operations from commercially available thiophenes, 2-bromobenzenesulfonyl chlorides and aryl bromides. In the first step, palladium-catalyzed desulfitative arylation using 2-bromobenzenesulfonyl chlorides allows the synthesis of thiophene derivatives, which are substituted at the C4 position by an aryl group containing an ortho-bromo substituent. Then, a palladium-catalyzed one-pot cascade intermolecular C5-arylation of thiophene using aryl bromides followed by intramolecular arylation led to the corresponding phenanthro[9,10-b]thiophenes in a single operation. In addition, PAHs containing two or three sulfur atoms, as well as both sulfur and nitrogen atoms, were also designed by this strategy. © 2016 American Chemical Society.

Domaines

Chimie
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Dates et versions

hal-01367240 , version 1 (15-09-2016)

Identifiants

Citer

W. Hagui, N. Besbes, E. Srasra, T. Roisnel, Jean-François Soulé, et al.. Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through Three Palladium-Catalyzed C-H Bond Arylations. Organic Letters, 2016, 18 (17), pp.4182--4185. ⟨10.1021/acs.orglett.6b01735⟩. ⟨hal-01367240⟩
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