Sulfonyl Halides
Sulfonyl Halides
Sulfonyl halides are a class of organic compounds in which a sulfonyl functional group is singly bonded to a halogen atom. These compounds readily react with other nucleophiles and hence they are useful laboratory, as well as, industrial reagents. Synthesis of sulfones by Friedal crafts reaction, reaction with amines to form sulfonamides, desulfonation of arylsulfonyl chlorides to form aryl chlorides are some of the chemical applications of sulfonyl halides. Sulfonyl halides are used in the preparation of sulfonate esters that are good leaving groups in organic synthesis.
Chiral sulfonyl chlorides find use as chiral derivatizing agents in the determination of the enantiomeric excess of alcohols and amines. Azo-chromophore bearing sulfonyl chlorides are known to be of use in instant photography as precursors. Sulfonyl chlorides, as efficient partners for arylation, have received considerable attention in coupling reactions including, but not limited to, Stille coupling, Suzuki coupling, and Sonogashira coupling. In recent years, sulfonyl chlorides have been shown to be efficient initiators of transition metal-catalyzed atom transfer radical polymerization.
They are widely used as important intermediates in the synthesis of dyes and pigments. They are also often employed as important drug intermediates. In medicinal chemistry, sulfonyl chlorides hold a unique position due to their ability to form complex biologically active sulfonamides with heterocyclic amines.
