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[Pd(Phbz)(X)(PPh3)] palladacycles promote the base-free homocoupling of arylboronic acids in air at room temperature

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Publication details

JournalRSC Advances
DateE-pub ahead of print - 9 Oct 2014
DatePublished (current) - 2014
Volume4
Pages (from-to)55305-55312
Early online date9/10/14
Original languageEnglish

Abstract

Homocoupling of arylboronic acids can be successfully achieved in commercial grade THF using [Pd(Phbz)(X)(PPh3)] palladacycles as catalysts (Phbz = N-phenylbenzaldimine; X = imidate or acetate). Symmetric biaryls were obtained in good yields working under mild conditions in an air atmosphere at room temperature. The reaction occurs without the addition of an exogenous base. The reaction conditions were optimized to provide the homocoupled products in excellent yield. Evidence for the transmetallation step being important for precatalyst activation has been gathered. The influence of electronic properties of the arylboronic acids on the outcome of the homocoupling reaction has been assessed through competition experiments.

    Research areas

  • Palladium, Catalysis, CROSS-COUPLING REACTION, BIARYLS

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