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Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3-triazoles.

ABSTRACT: Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

SUBMITTER: Culhane JC 

PROVIDER: S-EPMC3224852 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3-triazoles.

Culhane Jeffrey C JC   Fokin Valery V VV  

Organic letters 20110803 17

Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins. ...[more]

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