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Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands.
Nat Protoc. 2007; 2(12):3115-21.NP

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.

Authors+Show Affiliations

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18079711

Citation

Altman, Ryan A., and Stephen L. Buchwald. "Pd-catalyzed Suzuki-Miyaura Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands." Nature Protocols, vol. 2, no. 12, 2007, pp. 3115-21.
Altman RA, Buchwald SL. Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands. Nat Protoc. 2007;2(12):3115-21.
Altman, R. A., & Buchwald, S. L. (2007). Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands. Nature Protocols, 2(12), 3115-21.
Altman RA, Buchwald SL. Pd-catalyzed Suzuki-Miyaura Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands. Nat Protoc. 2007;2(12):3115-21. PubMed PMID: 18079711.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands. AU - Altman,Ryan A, AU - Buchwald,Stephen L, PY - 2007/12/15/pubmed PY - 2008/2/20/medline PY - 2007/12/15/entrez SP - 3115 EP - 21 JF - Nature protocols JO - Nat Protoc VL - 2 IS - 12 N2 - 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. SN - 1750-2799 UR - https://www.unboundmedicine.com/medline/citation/18079711/Pd_catalyzed_Suzuki_Miyaura_reactions_of_aryl_halides_using_bulky_biarylmonophosphine_ligands_ DB - PRIME DP - Unbound Medicine ER -