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Efficient Synthesis of Sterically Crowded Biaryls by Palladium-Phosphinous Acid-Catalyzed Cross-Coupling of Aryl Halides and Aryl Grignards
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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 °C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated.
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This article has been cited by 16 ACS Journal articles (5 most recent appear below).
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Ning Liu and Zhong-Xia WangThe Journal of Organic Chemistry2011 76 (24), 10031-10038A series of amido pincer complexes of nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer nickel complexes tested are active catalysts for the cross-coupling of aryl, heteroaryl, and vinyl chlorides with aryl ...
C–H Bond Arylations and Benzylations on Oxazol(in)es with a Palladium Catalyst of a Secondary Phosphine Oxide
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Lutz Ackermann, Sebastian Barfüsser, Christoph Kornhaass, and Anant R. KapdiOrganic Letters2011 Article ASAPAn air-stable, well-defined palladium complex derived from secondary phosphine oxide (SPO) (1-Ad)2P(O)H enabled efficient C–H bond functionalizations with ample scope, which set the stage for direct arylations and benzylations of (benz)oxazoles, as well ...
A Stereodynamic Probe Providing a Chiroptical Response to Substrate-Controlled Induction of an Axially Chiral Arylacetylene Framework
Daniel P. Iwaniuk and Christian WolfJournal of the American Chemical Society2011 133 (8), 2414-2417A Stereodynamic Probe Providing a Chiroptical Response to Substrate-Controlled Induction of an Axially Chiral Arylacetylene Framework
Daniel P. Iwaniuk and Christian WolfJournal of the American Chemical Society2011 133 (8), 2414-2417A stereodynamic probe containing a central 1,4-di(phenylethynyl)benzene rod and two 2-formylphenylethynyl branches has been prepared through a series of Sonogashira cross-coupling reactions with 62% overall yield. This CD silent diarylacetylene-based ...
Mechanistic Insights into C−S Cross-Coupling Reactions Catalyzed by Nickel Bis(phosphinite) Pincer Complexes
Jie Zhang, Christopher M. Medley, Jeanette A. Krause, and Hairong GuanOrganometallics2010 29 (23), 6393-6401Mechanistic Insights into C−S Cross-Coupling Reactions Catalyzed by Nickel Bis(phosphinite) Pincer Complexes
Jie Zhang, Christopher M. Medley, Jeanette A. Krause, and Hairong GuanOrganometallics2010 29 (23), 6393-6401Nickel bis(phosphinite) pincer complexes [2,6-(R2PO)2C6H3]NiCl (R = Ph, 1a; R = Me, 1b; R = iPr, 1c; R = tBu, 1d) show catalytic activity in cross-coupling of aryl iodides and aryl thiols. The optimal catalytic conditions involve 1 mol % of 1a and 2 equiv ...
Bidentate P, N−P Ligand for Nickel-Catalyzed Cross-Coupling of Aryl or Benzyl Chlorides with ArMgX
Raju Ghosh and Amitabha SarkarThe Journal of Organic Chemistry2010 75 (23), 8283-8286Bidentate P, N−P Ligand for Nickel-Catalyzed Cross-Coupling of Aryl or Benzyl Chlorides with ArMgX
Raju Ghosh and Amitabha SarkarThe Journal of Organic Chemistry2010 75 (23), 8283-8286A cross-coupling reaction of a variety of aryl, heteroaryl, and benzyl chlorides with ArMgX is catalyzed by 2 mol % of a nickel−phosphine complex prepared in situ from an equimolar amount of Ni(CH3CN)2Cl2 and ligand (L2) to yield products in excellent ...
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History
- Published In Issue January 04, 2008
- Received August 28, 2007
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