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Sulfate Click Chemistry

Researchers use SO2F groups as new links in simple selective reactions for forming carbon-heteroatom bonds

by Stephen K. Ritter
August 25, 2014 | A version of this story appeared in Volume 92, Issue 34

Credit: Angew. Chem. Int. Ed.
A bird’s nest of bisphenol A-polysulfate.
A BPA-sulfate polymer.
Credit: Angew. Chem. Int. Ed.
A bird’s nest of bisphenol A-polysulfate.

K. Barry Sharpless and his coworkers at Scripps Research Institute, in La Jolla, Calif., introduced the concept of click chemistry in the 1990s. Drawing largely on known reactions, the simple strategy involves using modular building blocks for the green synthesis of new compounds containing carbon-heteroatom linkages. Model reactions are copper-catalyzed azide-alkyne cycloadditions, which are useful in drug discovery, chemical biology research, and materials science. Sharpless and coworkers have now extended click chemistry by using SO2F functional groups prepared from sulfuryl fluoride (SO2F2) to make carbon-sulfate links, for example, in the synthesis of diarylsulfates (Angew. Chem. Int. Ed. 2014, DOI: 10.1002/anie.201309399). To demonstrate a potential commercial application, Sharpless, Valery V. Fokin, and colleagues clicked together SO2F2, bisphenol A, and various silyl chlorides to form polysulfates, a class of tough, high-clarity polymers related to polycarbonates that has not been widely studied because the macromolecules are difficult to make (Angew. Chem. Int. Ed. 2014, DOI: 10.1002/anie.201403758).


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