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Published on: August 19, 2012
Sulfur-Azide Exchange (SuAEx): A Click Reaction for Chemoselective Sulfonate Ester Formation
Ningning Song1, Linlin Xu1, Shengtao Ding1
1State Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China.
Abstract:
Here, we report sulfur-azide exchange (SuAEx), which facilitates the efficient synthesis of sulfonate esters via the reaction of sulfonyl azides with phenolic substrates under mild conditions. The reaction tolerates a wide range of functional groups. Notably, SuAEx displays a distinct preference for phenolic hydroxyls over aliphatic alcohols, providing orthogonality critical for complex molecular editing. Its utility is further demonstrated through iterative ligation strategies when combined with azide-alkyne cycloaddition reactions.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

