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Photochemical skeletal editing can move an acyl group between adjacent positions on a 2,3-dihydrobenzofuran ring, giving chemists access to a closely related constitutional isomer for structure–activity relationship (SAR) comparisons. The method offers a route to a molecular “matching pair”; it does not show that either compound is an effective medicine.
What pharmaceutical “matching pairs” are
In this work, a matching pair is two closely related molecules that differ in where an acyl group sits on the same ring framework. Comparing such structures can help researchers examine how a change in molecular structure relates to biological activity during an SAR campaign. The pair is a research tool, not a clinical result.
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Ryan T. Steele, Motohiro Fujiu, and Richmond Sarpong reported the reaction in a 2025 Science paper, “1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans”. A Chemistry World account published May 9, 2025, describes demonstrations on two compounds from recent SAR campaigns.
How the skeletal editing moves the acyl group
The starting materials are C2-acylated 2,3-dihydrobenzofurans. Under light, the ring rearranges through a highly electrophilic spirocyclopropane intermediate. The formal transformation exchanges the ring’s C2 and C3 positions, so the acyl group ends up at the adjacent position and the product is a constitutional isomer.
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In the acid-mediated sequence described by Chemistry World, dilute hydrochloric acid traps the spirocyclopropane intermediate; a subsequent basic step promotes halide elimination and ring re-formation. A complementary neutral route uses a metal halide salt to carry out the transformation in one step.
This is a specific rearrangement of a particular ring system, not a general technique for relocating any functional group on any drug molecule. The group identified other pharmaceutically relevant heterocycles, including indolines, as possible future directions—not demonstrated results of this study.
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Which reaction conditions suit which substrates?
The primary paper reports different irradiation wavelengths for different substrate classes. The Chemistry World account also compares the acidic and neutral condition sets by substrate features:
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| Condition set | Reported substrate fit | Reported irradiation |
|---|---|---|
| Acidic | Tolerated electron-donating and electron-withdrawing substituents. The account describes transposition of acyl groups, esters, amides, and carboxylic acids under acidic conditions. | Centered at 370 nm for a variety of aryl ketones; centered at 310 nm for carboxylic acids, esters, and amides, as reported in the primary paper. |
| Neutral | Favored substrates bearing basic groups, according to the Chemistry World account. | Not stated in the cited account; do not assume the acidic-condition wavelength applies. |
The wavelength and condition choices are substrate-specific experimental findings, not interchangeable settings or a guarantee that any UV source will reproduce the reaction. The researchers said the trends were still emerging and not fully understood. Sarpong told Chemistry World: “We do not fully understand the trends (which are still emerging) but it appears that in certain cases, the electronics of different portions of the substrate molecules makes them better behaved with one set of conditions over the other.”
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What the result does—and does not—establish
The study establishes a synthetic route to related molecular structures, including examples relevant to discovery-chemistry SAR campaigns. It does not establish improved biological activity, clinical efficacy, a faster drug-development process, or better patient outcomes. Those would require evidence beyond access to an isomeric structure.
The broader promise of molecular editing is an expert perspective rather than a result of this particular reaction. Bill Morandi of ETH Zürich told Chemistry World: “Functional group transpositions are highly underdeveloped but I think they could have a transformative impact on molecular editing, particularly when able to transpose polar groups [like] alcohols, amines [and] acyls,”
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