Media‐Driven Pd‐Catalyzed Reaction Cascades with 1,3‐Diynamides Leading Selectively to Either Indoles or Quinolines - Normandie Université Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2021

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

Résumé

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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Dates et versions

hal-03367794 , version 1 (08-04-2022)

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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, 2021, 60 (42), pp.22729-22734. ⟨10.1002/anie.202110221⟩. ⟨hal-03367794⟩
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