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Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings.
Chemistry. 2006 Jun 23; 12(19):5142-8.C

Abstract

The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading to very active catalytic species enabling the present catalytic transformations to be performed rapidly using very mild reaction conditions. Catalyst loadings can be as low as 10 ppm for the Buchwald-Hartwig aryl amination and 50 ppm for the Suzuki-Miyaura reaction.

Authors+Show Affiliations

Navarro O
Department of Chemistry, University of New Orleans, 2000 Lakeshore dr., New Orleans, LA 70148, USA.
Marion N
No affiliation info available
Mei J
No affiliation info available
Nolan SP
No affiliation info available

MeSH

Boronic AcidsBromidesCatalysisHalogensHeterocyclic CompoundsIndicators and ReagentsLigandsMagnetic Resonance SpectroscopyPalladiumTemperature

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

16628762

Citation

Navarro, Oscar, et al. "Rapid Room Temperature Buchwald-Hartwig and Suzuki-Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 12, no. 19, 2006, pp. 5142-8.
Navarro O, Marion N, Mei J, et al. Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings. Chemistry. 2006;12(19):5142-8.
Navarro, O., Marion, N., Mei, J., & Nolan, S. P. (2006). Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings. Chemistry (Weinheim an Der Bergstrasse, Germany), 12(19), 5142-8.
Navarro O, et al. Rapid Room Temperature Buchwald-Hartwig and Suzuki-Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings. Chemistry. 2006 Jun 23;12(19):5142-8. PubMed PMID: 16628762.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings. AU - Navarro,Oscar, AU - Marion,Nicolas, AU - Mei,Jianguo, AU - Nolan,Steven P, PY - 2006/4/22/pubmed PY - 2007/6/15/medline PY - 2006/4/22/entrez SP - 5142 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 12 IS - 19 N2 - The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading to very active catalytic species enabling the present catalytic transformations to be performed rapidly using very mild reaction conditions. Catalyst loadings can be as low as 10 ppm for the Buchwald-Hartwig aryl amination and 50 ppm for the Suzuki-Miyaura reaction. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/16628762/Rapid_room_temperature_Buchwald_Hartwig_and_Suzuki_Miyaura_couplings_of_heteroaromatic_compounds_employing_low_catalyst_loadings_ DB - PRIME DP - Unbound Medicine ER -