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Photochemical skeletal editing can rearrange certain 2,3-dihydrobenzofurans so an acyl group shifts from one ring position to the adjacent one. The result is a closely related constitutional isomer—a potential “matching pair” for comparing compounds in structure–activity relationship (SAR) research. It is a synthetic method, not evidence that either compound is an effective medicine.
What “pharmaceutical matching pairs” means
In this context, a matching pair is two closely related molecules that differ in the position of a functional group. Comparing such compounds can help researchers examine how molecular structure relates to biological activity. The pair is a tool for chemical and biological research; making it does not establish efficacy, safety, or clinical value.
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Ryan T. Steele, Motohiro Fujiu, and Richmond Sarpong reported a method for preparing these related structures by rearranging the carbon framework of selected 2,3-dihydrobenzofurans. Their study appeared in Science in 2025: “1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans”.
How the reaction moves an acyl group
The starting material is a 2-acylated 2,3-dihydrobenzofuran. Under irradiation, the reaction rearranges the ring by formally exchanging its C2 and C3 positions. This moves the acyl functionality to the neighboring position and produces a constitutional isomer: the molecular composition is related, but the connectivity differs.
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The proposed sequence passes through a highly electrophilic spirocyclopropane intermediate, which is intercepted by a halide nucleophile. In the acid-mediated sequence described by Chemistry World, dilute hydrochloric acid traps the intermediate; subsequent basic conditions promote halide elimination and re-form the ring. A parallel neutral route uses a metal halide salt to carry out the transformation in one step.
Which reaction conditions were reported
The primary report describes different irradiation wavelengths for different substrate classes. These are centered wavelengths for the reported conditions, not interchangeable settings or a guarantee that an arbitrary UV source will work.
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| Substrate class | Reported irradiation |
|---|---|
| A variety of aryl ketones | Centered at 370 nm |
| Carboxylic acids, esters, and amides | Centered at 310 nm |
Condition choice also depends on substrate features. The Chemistry World account says acidic conditions tolerated both electron-donating and electron-withdrawing substituents and accommodated acyls, esters, amides, and carboxylic acids. Neutral conditions favored substrates bearing basic groups. These are reported trends, not a universal substrate-selection rule: Sarpong said the team did not yet fully understand them.
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Preparing both members of a close structural pair can give discovery chemists a way to compare positional variants without designing two wholly independent synthetic routes. Chemistry World reported demonstrations on two compounds from recent SAR campaigns, indicating relevance to medicinal-chemistry research.
The result is a route to molecular variants, not proof of faster drug development, improved compounds, or better patient outcomes. The demonstrated chemistry is specific to 2,3-dihydrobenzofuran substrates and the reported functional-group scope; it should not be generalized to moving any group on any drug molecule. Extending the approach to other pharmaceutically relevant heterocycles, including indolines, was described as a research direction rather than a demonstrated result.
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Sarpong described the design idea as moving “a peripheral substituent” to an adjacent position by breaking and reforming bonds at the molecular core. Organic chemist Bill Morandi of ETH Zürich characterized functional-group transpositions as an underdeveloped area with potential for molecular editing, particularly for polar groups. That is a broader assessment of the field, not an experimental outcome of this specific reaction.
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