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Unconventional Reactivity with DABCO‐ Bis (sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines
Author(s) -
Le Bescont Julie,
BretonPatient Chloé,
Piguel Sandrine
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000112
Subject(s) - dabco , chemistry , reactivity (psychology) , steric effects , sulfone , sulfur dioxide , reagent , sulfur , aryl , functional group , octane , combinatorial chemistry , organic chemistry , medicinal chemistry , medicine , alkyl , alternative medicine , pathology , polymer
This work highlights the unexpected and unprecedented outcome of the reactivity with DABCO‐bis(sulfur dioxide). The use of this reagent led to the exclusive introduction of a sulfur atom on the C‐3 position of imidazopyridines instead of a sulfone group. The reaction methodology turned out to be robust, scalable and suitable for various imidazopyridines and aryl iodides both bearing substituents with different electronic and steric properties (38 examples). Beyond the fact that this synthetic method complements the previously reported protocols for sulfenylation reactions, this work is meant to underline the unconventional role of DABCO‐bis(sulfur dioxide).