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Palladium-Catalyzed Cascade sp(2) C-H Bond Functionalizations Allowing One-Pot Access to 4-Aryl-1,2,3,4-tetrahydroquinolines from N-Allyl-N-arylsulfonamides

Abstract : We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp(2))-C(sp(3)) bonds were formed via activation of C(sp(2))-H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.
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Submitted on : Thursday, July 13, 2017 - 12:00:47 PM
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Kedong Yuan, Jean-François Soulé, Vincent Dorcet, Henri Doucet. Palladium-Catalyzed Cascade sp(2) C-H Bond Functionalizations Allowing One-Pot Access to 4-Aryl-1,2,3,4-tetrahydroquinolines from N-Allyl-N-arylsulfonamides. ACS Catalysis, American Chemical Society, 2016, 6 (12), pp.8121-8126. ⟨10.1021/acscatal.6b02586⟩. ⟨hal-01438127⟩

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