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A 2017 report described a sulfur-centered alternative to the familiar azide–alkyne click reaction: thionyl tetrafluoride (SOF4) acts as a hub where successive substitutions can attach different groups in a three-dimensional, tetrahedral arrangement. The method offers a distinct way to connect molecules, but its proposed applications remain research directions, not evidence of clinical or commercial adoption.
What makes this approach different?
Many readers associate click chemistry with azide–alkyne coupling, which forms a triazole linkage between two components. The method reported by S. Li and colleagues instead uses sulfur(VI) fluoride exchange (SuFEx) reactions at a central sulfur atom. Rather than making only a linear connection between two partners, the sulfur center can serve as a hub for sequential attachments.
In the Chemistry World account, the researchers described the resulting arrangement as tetrahedral. The method was reported to allow up to three sequential connections from the SOF4 hub, with each connection introducing a distinct group. This is a change in both the chemistry used to make the linkage and the geometry available at the connecting point.
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The process begins with thionyl tetrafluoride gas. The reported substitutions depend on the functional group being attached and the catalytic conditions:
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- A primary amine displaces two fluorine atoms in the presence of a tertiary amine catalyst.
- A secondary amine, an amino acid, or a protected phenol can displace a third fluorine under basic catalysis.
- If protected phenols are used, the remaining fluorine can be displaced either by a secondary amine directly or by another protected phenol with a phosphazene base catalyst.
The account calls the sulfur(VI) fluoride compounds “sleeping beauties,” describing them as stable until exposure to tertiary amines, which can initiate controlled reactions. That phrase characterizes the reported chemistry; it is not a general guarantee of stability, safe handling, or suitability for a particular use.
Why the three-dimensional sulfur hub matters
A central hub that can accept several different attachments gives chemists another way to assemble complex molecules. John Moses, identified in the report as a member of the University of Nottingham team, said: “We demonstrate that three sequential reactions, each creating a unique connection, can be achieved with almost perfection.” He described the connections as extending “from a single sulfur hub into the 3D world, which is a first for a click connector.”
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The article points to biomolecule tagging, fragment-based drug discovery, and functional polymers as relevant applications or research directions. These examples indicate where researchers might explore the method; they do not establish that it has been adopted in clinical practice, commercial products, or routine manufacturing.
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The reported contribution is a new way to use sequential sulfur(VI) fluoride exchange to build multiple connections around a sulfur center. The Chemistry World article does not provide a full head-to-head performance comparison with azide–alkyne click chemistry, so it cannot establish that this approach is faster, more efficient, safer, or better for a particular application.
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It also reports that, in February 2017, SOF4 was not commercially available and that the team was working with a Chinese company toward a ton-scale process. That is a historical availability statement only. Current supply, applicable handling requirements, and regulatory restrictions are not established by that report; they must be checked with current, authoritative sources before any practical work.
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The Chemistry World account covers the work by S. Li et al., published in Angewandte Chemie International Edition in 2017 (DOI: 10.1002/anie.201611048). Eric Anslyn of the University of Texas at Austin called it “a nice continuation of work from the Sharpless lab on extensions of click chemistry,” noting its potential for “more versatile methods with controllable three-dimensional control at the conjugating agent.” He also said simple assembly around a single core should help in fragment-based drug discovery. Those comments describe the method’s promise, not proof of downstream adoption.
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Sources: Chemistry World’s report on the sulfur-centered click chemistry method; S. Li et al., DOI 10.1002/anie.201611048.
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