Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
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Updated: Jul 9, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Ryan A Altman1, Stephen L Buchwald
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.
Abstract:
The following protocol describes the application of a highly active Pd-based catalyst system in the Suzuki-Miyaura cross-coupling reaction of arylboronic acids with aryl chlorides to provide biaryl compounds. The general procedure includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (GC and TLC) and a procedure for the isolation, purification and characterization of the anticipated product. Reagents and catalyst precursors can be manipulated in the air; however, the cross-coupling reactions must be performed in an inert atmosphere. Two Suzuki-Miyaura reactions are included in the text as representative examples of these procedures. Although the reactions can proceed in less than 5 min, the protocols, including workup, generally take 6-30 h to be completed.
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