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Issue 8, 2011
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Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran

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Abstract

A straightforward chemoselective protection of anilines as N-TBS derivatives is described by using a suitable deprotonation of the amine with methyllithium in the environmentally friendly and safer substitute of THF, 2-methyltetrahydrofuran, under exceptional mild reaction conditions (0 °C, 30 min). Interestingly, the protecting group maybe cleaved efficiently by simple treatment of N-TBS-anilines with silica gel in ethanolwater.

Graphical abstract: Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran

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Publication details

The article was received on 18 May 2011, accepted on 06 Jun 2011 and first published on 07 Jul 2011


Article type: Communication
DOI: 10.1039/C1GC15574A
Citation: Green Chem., 2011,13, 1986-1989
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    Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran

    V. Pace, A. R. Alcántara and W. Holzer, Green Chem., 2011, 13, 1986
    DOI: 10.1039/C1GC15574A

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