A Practical Protocol for Three-Component, One-Pot, Stepwise Sonogashira-Heterocyclization-Heck Couplings

A Practical Protocol for Three-Component, One-Pot, Stepwise Sonogashira--Heterocyclization-Heck Couplings. -A stepwise protocol is developed for the three-component process using halobenzamides, alkynes, and ethyl acrylate. The cyclization-intermolecular Heck coupling cascade of the initially formed 2-alkynylbenzamides with ethyl acrylate provides cyclic amidates in a 6-endo-selective manner. The extension of this protocol to phenol and aniline type substrates allows the preparation of benzofurane and indole derivatives. -(MADICH, Y.; DENIS, J. G.; ORTEGA, A.; MARTINEZ, C.; MATRANE, A.; BELACHEMI, L.; DE LERA, A. R.; ALVAREZ, R.; AURRECOECHEA*, J. M.; Synthesis 45 (

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ChemInform Abstract: A Practical Protocol for Three‐Component, One‐Pot, Stepwise Sonogashira—Heterocyclization—Heck Couplings.

Madich

Denis

Ortega

et al. 2013

ChemInform

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Palladium‐Catalyzed Regioselective 5‐exo‐O‐Cyclization/Oxidative Heck Cascades from o‐Alkynylbenzamides and Electron‐Deficient Alkenes

2014

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A Pd‐catalyzed 5‐exo‐selective oxycyclization/oxidative Heck coupling cascade is described, starting from readily available ortho‐alkynylbenzamides and functionalized olefins. The key to a high regioselectivity in the cyclization step is the choice of catalyst and/or additives. Thus, Pd(OAc)2 provides the desired 5‐exo products predominantly, whereas with PdCl2 or Pd(TFA)2, the corresponding 6‐endo products prevail. The subsequent oxidative Heck‐type coupling takes place stereoselectively with the very predominant formation of E isomers, leading to an effective preparation of structurally diverse carbonyl‐substituted allylideneisobenzofuranimines.

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Nucleophilic Cyclization of o‐Alkynylbenzamides Promoted by Iron(III) Chloride and Diorganyl Dichalcogenides: Synthesis of 4‐Organochalcogenyl‐1H‐isochromen‐1‐imines

2015

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We have developed a method for the preparation 4‐organochalcogenyl‐1H‐isochromen‐1‐imines from o‐alkynylbenzamides. This electrophile‐promoted nucleophilic cyclization achieved by treatment with a combination of iron salts and diorganyl dichalcogenides. FeCl3 and diorganyl dichalcogenides reacted with o‐alkynylbenzamides under aerobic conditions at room temperature and in the absence of additives to give 4‐organochalcogenyl‐1H‐isochromen‐1‐imines in good yields and with good selectivities. The reaction took place with 0.5 equiv. of the diorganyl dichalcogenides, which demonstrates that both halves of the diorganyl dichalcogenides (RYYR → 2RY) were incorporated into the final product. Mechanistic studies suggested that the regioselectivity of the cyclization is governed by a seleniranium ion, a key intermediate formed by the electrophilic addition of the organochalcogen moiety to the carbon–carbon triple bond. The utility of the 4‐organochalcogenyl‐1H‐isochromen‐1‐imines was also demonstrated by their application as starting materials in Suzuki and Sonogashira cross‐coupling reactions.

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A Practical Protocol for Three-Component, One-Pot, Stepwise Sonogashira-Heterocyclization-Heck Couplings

Cited by 10 publications

References 24 publications

ChemInform Abstract: A Practical Protocol for Three‐Component, One‐Pot, Stepwise Sonogashira—Heterocyclization—Heck Couplings.

ChemInform Abstract: A Practical Protocol for Three‐Component, One‐Pot, Stepwise Sonogashira—Heterocyclization—Heck Couplings.

Palladium‐Catalyzed Regioselective 5‐exo‐O‐Cyclization/Oxidative Heck Cascades from o‐Alkynylbenzamides and Electron‐Deficient Alkenes

Nucleophilic Cyclization of o‐Alkynylbenzamides Promoted by Iron(III) Chloride and Diorganyl Dichalcogenides: Synthesis of 4‐Organochalcogenyl‐1H‐isochromen‐1‐imines

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