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. 2011 Sep 16;13(18):4850-3.
doi: 10.1021/ol201930e. Epub 2011 Aug 19.

Palladium-catalyzed alkylation of ortho-C(sp2)-H bonds of benzylamide substrates with alkyl halides

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Palladium-catalyzed alkylation of ortho-C(sp2)-H bonds of benzylamide substrates with alkyl halides

Yingsheng Zhao et al. Org Lett. .

Abstract

A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp(2))-H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of β-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.

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