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Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards.
J Org Chem. 2008 Jan 04; 73(1):162-7.JO

Abstract

A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada-Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87-98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides at -20 degrees C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated.

Authors+Show Affiliations

Wolf C
Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu
Xu H
No affiliation info available

MeSH

Biphenyl CompoundsCatalysisHydrocarbons, HalogenatedLigandsMolecular StructureOrganometallic CompoundsPalladiumPhosphorus AcidsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18052388

Citation

Wolf, Christian, and Hanhui Xu. "Efficient Synthesis of Sterically Crowded Biaryls By Palladium-phosphinous Acid-catalyzed Cross-coupling of Aryl Halides and Aryl Grignards." The Journal of Organic Chemistry, vol. 73, no. 1, 2008, pp. 162-7.
Wolf C, Xu H. Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards. J Org Chem. 2008;73(1):162-7.
Wolf, C., & Xu, H. (2008). Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards. The Journal of Organic Chemistry, 73(1), 162-7.
Wolf C, Xu H. Efficient Synthesis of Sterically Crowded Biaryls By Palladium-phosphinous Acid-catalyzed Cross-coupling of Aryl Halides and Aryl Grignards. J Org Chem. 2008 Jan 4;73(1):162-7. PubMed PMID: 18052388.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards. AU - Wolf,Christian, AU - Xu,Hanhui, Y1 - 2007/12/06/ PY - 2007/12/7/pubmed PY - 2008/3/20/medline PY - 2007/12/7/entrez SP - 162 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 1 N2 - A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada-Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87-98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides at -20 degrees C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18052388/Efficient_synthesis_of_sterically_crowded_biaryls_by_palladium_phosphinous_acid_catalyzed_cross_coupling_of_aryl_halides_and_aryl_grignards_ DB - PRIME DP - Unbound Medicine ER -