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Highly selective palladium-catalyzed cross-coupling of secondary alkylzinc reagents with heteroaryl halides.

ABSTRACT: The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.

SUBMITTER: Yang Y 

PROVIDER: S-EPMC4156254 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Highly selective palladium-catalyzed cross-coupling of secondary alkylzinc reagents with heteroaryl halides.

Yang Yang Y   Niedermann Katrin K   Han Chong C   Buchwald Stephen L SL  

Organic letters 20140825 17

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive e  ...[more]

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