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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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Supplementary files

Article information


Submitted
02 Feb 2011
Accepted
17 Mar 2011
First published
18 Apr 2011

Green Chem., 2011,13, 1778-1783
Article type
Paper

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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