Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer

Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient interme...

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Bibliographic Details
Published in:Synlett 2015-04, Vol.26 (7), p.953-959
Main Authors: Panteleev, Jane, Maguire, Robert J., Kung, Daniel W.
Format: Article
Language:English
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Summary:Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N -Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1379961