N-(tert-Butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide: A Convenient Sulfamoylation Reagent for Alcohols

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (10), p.2626-2629
Main Authors: Armitage, Ian, Berne, Alexander M, Elliott, Eric L, Fu, Mingkun, Hicks, Frederick, McCubbin, Quentin, Zhu, Lei
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Amines
Indicators and Reagents
Molecular Structure
Phenols
Sulfones - chemistry
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Summary:A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ≫ tertiary). The reagent’s utility as a selective sulfamoylation reagent with polyols is also demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3009683