Unexpected Cross-Coupling Reaction between o-Chloroaryl Ketones and Organomanganese Reagents

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Abstract

Alkyl- and arylmanganese reagents react with o-chloro or o-bromoaryl ketones to give the substituted ketones in high yields. The cross-coupling reaction is performed under mild conditions (−60 to +40 °C, 30 min to 4 h) and takes place with excellent chemoselectivity.

Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

• 

  Preparation of Functionalized Organomanganese(II) Reagents by Direct Insertion of Manganese to Aromatic and Benzylic Halides

  Zhihua Peng and Paul Knochel
  Organic Letters2011 Article ASAP

  • Preparation of Functionalized Organomanganese(II) Reagents by Direct Insertion of Manganese to Aromatic and Benzylic Halides

    Zhihua Peng and Paul Knochel
    Organic Letters2011 Article ASAP

    Functionalized arylmanganese compounds were prepared using commercial manganese powder in the presence of LiCl and catalytic amounts of both 2.5% InCl3 and 2.5% PbCl2 (THF, 0–50 °C). In addition, benzylic manganese reagents are obtained at 25 °C in ca. 70–...

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• 

  Chemistry of Organomanganese(II) Compounds

  Gérard Cahiez, Christophe Duplais and Julien Buendia
  Chemical Reviews2009 109 (3), 1434-1476

  • Chemistry of Organomanganese(II) Compounds

    Gérard Cahiez, Christophe Duplais and Julien Buendia
    Chemical Reviews2009 109 (3), 1434-1476
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Manganese-Catalyzed Cross-Coupling Reaction between Aryl Grignard Reagents and Alkenyl Halides

  Gérard Cahiez, Olivier Gager and Fabien Lecomte
  Organic Letters2008 10 (22), 5255-5256

  • Manganese-Catalyzed Cross-Coupling Reaction between Aryl Grignard Reagents and Alkenyl Halides

    Gérard Cahiez, Olivier Gager and Fabien Lecomte
    Organic Letters2008 10 (22), 5255-5256

    Aryl Grignard reagents react stereospecifically with alkenyl halides in the presence of manganese chloride (10%) to afford good yields of cross-coupling products.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Unexpected Stereodynamic Consequences of the Restricted Rotations in ortho-Acyl- and ortho-Vinyl Biphenyls

  Lodovico Lunazzi, Andrea Mazzanti, and Mirko Minzoni
  The Journal of Organic Chemistry2006 71 (25), 9297-9301

  • Unexpected Stereodynamic Consequences of the Restricted Rotations in ortho-Acyl- and ortho-Vinyl Biphenyls

    Lodovico Lunazzi, Andrea Mazzanti, and Mirko Minzoni
    The Journal of Organic Chemistry2006 71 (25), 9297-9301

    Surprisingly, the aryl−aryl rotation barriers of biphenyl derivatives ortho-substituted by the “small” HCO and HCCH2 groups (10.0 and 8.4 kcal mol-1, respectively) were found greater than those observed in biphenyls ortho-substituted by the “large” t-BuCO ...

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