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

Abstract : 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01367240
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Submitted on : Thursday, September 15, 2016 - 5:17:57 PM
Last modification on : Friday, July 10, 2020 - 4:24:33 PM

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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, American Chemical Society, 2016, 18 (17), pp.4182--4185. ⟨10.1021/acs.orglett.6b01735⟩. ⟨hal-01367240⟩

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