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Synthesis

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 | APPEARED IN VOLUME 92, ISSUE 34

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Credit: Angew. Chem. Int. Ed.
A bird’s nest of bisphenol A-polysulfate.
09234-scicon-polysulfatecxd.jpg
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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Comments
Auntie Markovnikov (August 25, 2014 2:24 PM)
And why is this chemistry considered "green"? Every monomer unit consumes two moles of R3SiCl and generates two moles each of R3SiF and hydrochloride waste (would be helpful if the graphic showed a complete balanced reaction). SO2F2 is a potent greenhouse gas.
Steve Ritter (September 4, 2014 4:15 PM)
Click chemistry in general is efficient and atom-economical, so it is considered a green reaction. But remember green is a relative term. With in situ generation of SO2F2, making aryl sulfates seems good. True, the example of making a polysulfate does not meet green criteria, but the article does not call the polymerization green.

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