Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer
- Resource Type
- Authors
- Robert John Maguire; Daniel W. Kung; Jane Panteleev
- Source
- Synlett. 26:953-959
- Subject
- In situ
Sulfonyl
chemistry.chemical_classification
Primary (chemistry)
education
Organic Chemistry
chemistry.chemical_element
Alcohol
Alkylation
Nitrogen
chemistry.chemical_compound
chemistry
SN2 reaction
Organic chemistry
Alkyl
- Language
- ISSN
- 1437-2096
0936-5214
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.