A Green N-Detosylation of Indoles and Related Heterocycles Using Phase Transfer Catalysis

A Green N-Detosylation of Indoles and Related Heterocycles Using Phase Transfer Catalysis

A practical method for the N-detosylation of indoles and related heterocycles with KOH in THF and water in the presence of a phase transfer catalyst is described. Using a nonalcoholic solvent, this method prevents the formation of toxic alkyl p-toluenesulfonate and consequently eliminates the format...

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Veröffentlicht in:Organic process research & development 2008-07, Vol.12 (4), p.778-780
Hauptverfasser: Liu, Yugang, Shen, Lichun, Prashad, Mahavir, Tibbatts, Jessica, Repič, Oljan, Blacklock, Thomas J
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container_issue 4
container_start_page 778
container_title Organic process research & development
container_volume 12
creator Liu, Yugang
Shen, Lichun
Prashad, Mahavir
Tibbatts, Jessica
Repič, Oljan
Blacklock, Thomas J
description A practical method for the N-detosylation of indoles and related heterocycles with KOH in THF and water in the presence of a phase transfer catalyst is described. Using a nonalcoholic solvent, this method prevents the formation of toxic alkyl p-toluenesulfonate and consequently eliminates the formation of even traces of N-alkyl byproduct. This green method is particularly useful for indoles bearing electron-withdrawing groups and for azaindoles.
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title A Green N-Detosylation of Indoles and Related Heterocycles Using Phase Transfer Catalysis
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