4.5 Article

Propylphosphonic Anhydride (T3P®)-Mediated One-Pot Rearrangement of Carboxylic Acids to Carbamates

Journal

SYNTHESIS-STUTTGART
Volume -, Issue 9, Pages 1477-1483

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1259964

Keywords

propylphosphonic anhydride; Curtius rearrangement; carbamates; peptide coupling agents; azidotrimethylsilane

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A simple one-pot conversion of carboxylic acids to carbamates is achieved by propylphosphonic anhydride (T3P (R)) in combination with azidotrimethylsilane and an alcohol via the Curtius rearrangement. Besides diverse primary to tertiary alcohols, the reaction tolerated a wide scope of aromatic, heterocyclic, and aliphatic carboxylic acids which underwent rearrangement in excellent yields.

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