Protocol abstract
Nature Protocols 2, - 3115 - 3121 (2007)
Published online: 6 December 2007 | doi:10.1038/nprot.2007.411
Subject Category: Synthetic chemistry
Pd-catalyzed Suzuki–Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Ryan A Altman1 & Stephen L Buchwald1
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.
- Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.
Correspondence to: Stephen L Buchwald1 e-mail: sbuchwal@mit.edu
nature-products
A-Z product listing
- Air-tight microsyringes (100–500
l(Hamilton) - Anhydrous solvents including toluene, tetrahydrofuran (THF) and n- and s-butanol(Aldrich)
- Aryl halides(Acros)
- Basic alumina(EMD Chemicals Inc.)
- Boronic acids(Sigma-Aldrich)
- Büchner funnel with vacuum adapter(Chemglass)
