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Media‐Driven Pd‐Catalyzed Reaction Cascades with 1,3‐Diynamides Leading Selectively to Either Indoles or Quinolines

Abstract : Divergent Pd-catalyzed reaction cascades with various 1,3-diynamides yielding either 2-amino-3-alkynylindoles or 2-amino-4-alkenylquinolines were established. Omitting or adding TBAF (tetrabutylammonium fluoride) to the reaction of N,N-(2-iodophenyl)(4-toluenesulfonyl)-1,3-diynamides with secondary or primary amines in the presence of KOH in THF and catalytic amounts of Pd(PPh3)4 completely changed the outcome of the reaction. In absence of TBAF, 2-amino-3-alkynylindoles were the sole products, while the presence of TBAF switched the product formation to 2-amino-4-alkenylquinolines. Deuterium labeling proceeded selectively at the C3 and C11 positions of the 2-amino-4-alkenylquinoline products and this suggests the unprecedented formation of [4]cumulenimines from 1,3-diynamides as reactive key intermediates.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-03367794
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Submitted on : Wednesday, October 6, 2021 - 1:57:19 PM
Last modification on : Thursday, October 7, 2021 - 3:40:04 AM

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Illia Lenko, Alexander Mamontov, Carole Alayrac, Rémi Legay, Bernhard Witulski. Media‐Driven Pd‐Catalyzed Reaction Cascades with 1,3‐Diynamides Leading Selectively to Either Indoles or Quinolines. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (42), pp.22729-22734. ⟨10.1002/anie.202110221⟩. ⟨hal-03367794⟩

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