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Domino [Pd]-Catalysis: Heck followed by decarboxylative Sonogashira couplings under microwave irradiation in aqueous medium

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Abstract A copper free [Pd]-catalyzed domino intramolecular Heck and intermolecular decarboxylative Sonogashira couplings, for the synthesis of alkyne bearing heterocyclic compounds with a quaternary carbon atom, is described. Notably, this… Click to show full abstract

Abstract A copper free [Pd]-catalyzed domino intramolecular Heck and intermolecular decarboxylative Sonogashira couplings, for the synthesis of alkyne bearing heterocyclic compounds with a quaternary carbon atom, is described. Notably, this dual bond forming strategy is successful in water solvent, under microwave irradiation. This one-pot operation enabled the formation of a variety of dihydrobenzofurans, indolines and oxindoles, in very good to near quantitative yields. Notably, unlike earlier reports, the present strategy is successful in delivering the products with short alkyl substituents on acetylene carbon, which is first of its kind.

Keywords: heck; sonogashira couplings; decarboxylative sonogashira; domino; microwave irradiation

Journal Title: Journal of Organometallic Chemistry
Year Published: 2019

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