Title of article :
Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst
Author/Authors :
Upadhyaya، نويسنده , , Dharita J. and Barge، نويسنده , , Alessandro and Stefania، نويسنده , , Rachele and Cravotto، نويسنده , , Giancarlo، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2007
Abstract :
A simple, rapid, and efficient protocol for the chemoselective N-Boc protection of amines using sulfamic acid as catalyst is described. N-Boc protection of various structurally diverse aliphatic, aromatic, alicyclic, and heterocyclic amines (1°, 2°, 3°) was carried out with (Boc)2O using sulfamic acid as catalyst (5 mol %) at room temperature under solventless conditions. The advantages of this method are simplicity, shorter reaction times (1–15 min), a cost-effective catalyst, and excellent isolated yields (90–100%); it is also environmentally benign. Moreover, the combined use of ultrasound and sulfamic acid achieves a synergic effect that is especially marked in the N-Boc protection of deactivated (sterically hindered and electron-deficient) amines. The catalyst possesses distinct advantages: ease of handling, cleaner reactions, high activity, and excellent chemoselectivity.
Keywords :
Ultrasound , solvent-free reaction , Sulfamic acid , N-Boc protection , Recyclable catalyst
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters