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Repair Windows errors before they cause bigger problemsFix Now →Fix the driver behind crashes, sound loss and screen glitchesFind Drivers →Clear out junk files and repair common Windows errorsFree Scan →Yes. A 2023 study showed that a carefully designed pair of radicals can break unactivated aliphatic C–H bonds and convert them into aminoxylated products. Changing the donor can shift which carbon site reacts. The result is a proof-of-concept synthetic method, not evidence of routine industrial use.
What the reaction does
Aliphatic C–H bonds are common in organic molecules but can be difficult to functionalize selectively. Lu, Ju and colleagues reported a method in which a disilazide donor and an N-oxoammonium acceptor undergo single-electron transfer (SET), generating a frustrated radical pair. The pair enables cleavage of a C–H bond and formation of an aminoxylated product. The study appeared in Nature, volume 619, pages 514–520, on 5 July 2023 (primary study).
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Here, “unactivated” refers to aliphatic C(sp3)–H bonds that are not first given a special activating group for the reaction. The paper’s central result is that donor design can influence whether a primary, secondary or tertiary C–H site is functionalized.
How a frustrated radical pair cleaves a C–H bond
In a conventional reaction, two radicals may recombine to make a closed-shell bond. In a frustrated radical pair (FRP), steric crowding or weak association can keep the two radicals from simply annihilating each other. The term is related to frustrated Lewis pairs, but the mechanism here is not the canonical heterolytic activation often associated with FLP chemistry: the key step is single-electron transfer followed by radical chemistry.
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- Generate the pair. SET between the disilazide donor and N-oxoammonium acceptor produces two radicals with complementary roles.
- Remove hydrogen. One radical acts as a hydrogen-atom acceptor (HAA), taking a hydrogen atom from the alkane. This hydrogen-atom transfer (HAT) leaves a carbon-centered alkyl radical.
- Capture the carbon radical. The persistent radical in the pair traps the alkyl radical, yielding an aminoxylated product.
This cooperative sequence matters: one radical helps break the C–H bond, while the other captures the carbon radical that results. The approach is not simply a matter of adding a radical reagent and expecting it to activate every alkane.
How donor choice changes the reaction site
The reported isopentane comparison illustrates the effect of donor structure. The percentages below are site-selectivity figures for that particular substrate and reaction context—not product yields or general performance guarantees.
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| Donor | Reported favored site in isopentane | Reported selectivity |
|---|---|---|
| LiHMDS | Secondary C–H | 50% |
| LiHPDS | Primary C–H | 93% |
The study describes donor tuning as a way to tailor reactivity toward tertiary, secondary or primary C–H bonds. These two isopentane results demonstrate that possibility in a specific example; they do not establish that either donor will give the same selectivity with other substrates.
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The authors report mechanistic studies supporting formation and involvement of the radical pairs, and they demonstrate product derivatization. Together, those results establish a synthetic reaction design for aliphatic C–H functionalization. They do not, on their own, establish broad industrial adoption, routine process-scale deployment, universal substrate scope, or superiority to other C–H functionalization methods.
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A 2023 specialist review treats FRP synthetic applications as an emerging area and surveys a wider range of reaction types (review of frustrated radical pairs in organic synthesis). Comparing this method with directed or transition-metal approaches would require matched evidence on substrate scope, site selectivity, product utility and practical conditions; the reported selectivity examples alone do not support a general ranking.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Where to read the study
The primary article is titled “Regioselective aliphatic C–H functionalization using frustrated radical pairs.” Its indexed record summarizes the study and the isopentane selectivity examples (PubMed record). For operational details such as reagent equivalents and conditions, consult the paper and its Supplementary Information rather than inferring a recipe from the selectivity data.
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