Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates

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Abstract

We previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

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This article has been cited by 16 ACS Journal articles (5 most recent appear below).

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  Direct Aminoalkylation of Arenes, Heteroarenes, and Alkenes via Ni-Catalyzed Negishi Cross-Coupling Reactions

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  The Journal of Organic Chemistry2011 76 (21), 8891-8906

  • Direct Aminoalkylation of Arenes, Heteroarenes, and Alkenes via Ni-Catalyzed Negishi Cross-Coupling Reactions

    Laurin Melzig, Teresa Dennenwaldt, Andrey Gavryushin, and Paul Knochel
    The Journal of Organic Chemistry2011 76 (21), 8891-8906

    A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a ...

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

  Hybrid Thiophosphoryl–Benzothiazole Palladium SCN-Pincer Complexes: Synthesis and Effect of Structure Modifications on Catalytic Performance in the Suzuki Cross-Coupling

  Vladimir A. Kozlov, Diana V. Aleksanyan, Yulia V. Nelyubina, Konstantin A. Lyssenko, Pavel V. Petrovskii, Andrei A. Vasil’ev, and Irina L. Odinets
  Organometallics2011 Article ASAP

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    Vladimir A. Kozlov, Diana V. Aleksanyan, Yulia V. Nelyubina, Konstantin A. Lyssenko, Pavel V. Petrovskii, Andrei A. Vasil’ev, and Irina L. Odinets
    Organometallics2011 Article ASAP

    The novel hybrid pincer-type ligands 3, 6, 9, and 11, bearing, as donating sites, a thiophosphoryl group and an imine moiety of the benzothiazole ring bound either directly to the central benzene core or attached to the latter one via O or NH linkers, ...

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

  Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

  Jessica Raushel, Deidre L. Sandrock, Kanth V. Josyula, Deborah Pakyz, and Gary A. Molander
  The Journal of Organic Chemistry2011 76 (8), 2762-2769

  • Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

    Jessica Raushel, Deidre L. Sandrock, Kanth V. Josyula, Deborah Pakyz, and Gary A. Molander
    The Journal of Organic Chemistry2011 76 (8), 2762-2769

    A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction ...

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

  Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates

  Gary A. Molander, Nicolas Fleury-Brégeot, and Marie-Aude Hiebel
  Organic Letters2011 13 (7), 1694-1697

  • Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates

    Gary A. Molander, Nicolas Fleury-Brégeot, and Marie-Aude Hiebel
    Organic Letters2011 13 (7), 1694-1697

    Sulfonamidomethyltrifluoroborates were successfully synthesized and cross-coupled with a wide range of aryl and heteroaryl chlorides, allowing the construction of a sulfonamidomethyl aryl linkage through a new disconnection, thus offering a new way to ...

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

  Cross-Coupling of Mesylated Phenol Derivatives with Potassium Ammonio- and Amidomethyltrifluoroborates

  Gary A. Molander and Floriane Beaumard
  Organic Letters2011 13 (5), 1242-1245

  • Cross-Coupling of Mesylated Phenol Derivatives with Potassium Ammonio- and Amidomethyltrifluoroborates

    Gary A. Molander and Floriane Beaumard
    Organic Letters2011 13 (5), 1242-1245

    A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp2−Csp3 Suzuki−Miyaura cross-coupling with potassium ammonio- and amidomethyltrifluoroborates to afford the corresponding products in high yields.

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

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