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Yes. A 2023 study showed that a carefully designed pair of radicals can break unactivated aliphatic C–H bonds and install an aminoxyl group. Changing the donor structure shifted which carbon site reacted. The result is a proof of concept in synthetic chemistry—not evidence of routine industrial use.
What the reaction does
In conventional organic molecules, an unactivated C–H bond is not already equipped with a directing group that makes a particular site easy to functionalize. The study by Lu, Ju and colleagues used single-electron transfer (SET) between a disilazide donor and an N-oxoammonium acceptor to generate a frustrated radical pair. The pair enables cleavage of an aliphatic C(sp3)–H bond and formation of an aminoxylated product. The authors’ paper appeared in Nature on 5 July 2023, volume 619, pages 514–520.
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How a frustrated radical pair cleaves a C–H bond
From donor and acceptor to two radicals
Frustrated Lewis pairs (FLPs) are donor–acceptor combinations whose components are hindered from forming an ordinary Lewis adduct. In some systems, instead of bonding in the usual way, the components exchange an electron and form radicals. In the 2023 reaction, the selected pair produces a transient radical that can accept a hydrogen atom and a more persistent radical that can capture the carbon-centered radical formed by C–H cleavage.
Hydrogen transfer followed by radical capture
The hydrogen-atom-accepting radical removes hydrogen from the alkane through hydrogen-atom transfer (HAT). That step leaves a carbon-centered alkyl radical. The persistent radical traps it, leading to the aminoxylated product. Steric crowding and weak association help keep the two radicals from simply recombining with each other.
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This is a homolytic radical sequence, not the canonical heterolytic activation often associated with FLP chemistry. A specialist perspective surveys frustrated radical pairs and their broader synthetic chemistry: “Frustrated Radical Pairs in Organic Synthesis”.
How donor design changes the site selected
The paper reports that changing the donor can favor tertiary, secondary or primary aliphatic C–H bonds. Its isopentane example illustrates the effect:
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| Donor used | Reported isopentane site preference | What the figure means |
|---|---|---|
| LiHMDS | 50% secondary-site selectivity | Selectivity in the reported reaction example; not product yield or a general performance figure. |
| LiHPDS | 93% primary-site selectivity | Selectivity in the reported reaction example; not product yield or a general performance figure. |
These numbers describe site selectivity for that substrate and reaction context. They should not be treated as universal constants or as a head-to-head measure of yield. The authors state that tuning donor structure can control regioselectivity and tailor reactivity toward tertiary, secondary or primary C–H bonds. The indexed study record includes further reaction details, but operational conditions should be taken from the primary paper and its Supplementary Information: PubMed record PMID 37407819.
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The study presents a synthetic method for functionalizing unactivated aliphatic C(sp3)–H bonds, supported by mechanistic studies of radical-pair formation and involvement. It also reports product derivatization. This makes the work a research demonstration of a way to combine hydrogen-atom transfer with radical capture.
It does not establish that the method is broadly applicable to every alkane, safer or more efficient than all other C–H functionalization strategies, or deployed routinely at manufacturing scale. The available evidence supports describing frustrated-radical-pair synthesis as an emerging area rather than a mature industrial process. For contemporary news context on the result, see Chemistry World’s 10 July 2023 coverage.
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