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Issue 7, 2011
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Synthesis of nucleoside analogues in a ball mill: fast, chemoselective and high yielding acylation without undesirable solvents

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Abstract

The chemoselective acylation of primary aliphatic amines has been achieved in under ten minutes (and for aromatic amines under 120 min) using vibration ball-milling, avoiding undesirable solvents which are typically employed for such reactions (e.g.DMF). Under optimised conditions, the synthesis of amides in the presence of both primary and secondary alcohol functions was achieved in high to excellent yields (65–94%). Overall, the methods described have significant practical advantages over conventional approaches based upon bulk solvents including greater yields, higher chemoselectivity and easier product separation.

Graphical abstract: Synthesis of nucleoside analogues in a ball mill: fast, chemoselective and high yielding acylation without undesirable solvents

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Publication details

The article was received on 02 Feb 2011, accepted on 17 Mar 2011 and first published on 18 Apr 2011


Article type: Paper
DOI: 10.1039/C1GC15131B
Green Chem., 2011,13, 1778-1783

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    Synthesis of nucleoside analogues in a ball mill: fast, chemoselective and high yielding acylation without undesirable solvents

    F. Ravalico, S. L. James and J. S. Vyle, Green Chem., 2011, 13, 1778
    DOI: 10.1039/C1GC15131B

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