4.4 Article

Amide Activation by Tf2O: Reduction of Amides to Amines by NaBH4 under Mild Conditions

Journal

SYNLETT
Volume -, Issue 12, Pages 1829-1832

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1258111

Keywords

reduction; amides; amines; amide activation; triflic anhydride

Funding

  1. NSF of China [20832005]
  2. National Basic Research Program (973 Program) of China [2010CB833200]

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An expeditious and practical method for the reduction of amides to amines is reported. The method is consisted of activation of amides with Tf2O followed by reduction with sodium borohydride in THF at room temperature. Various amides/lactams gave the corresponding amines in good to excellent yields, even with hindered amides and secondary amides. This method also presents other advantages such as TBDPS-group tolerance, short reaction time, simple workup and purification procedure.

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