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1Repair Windows errors before they cause bigger problems2Scan for outdated or missing drivers - takes under a minute3Clear out junk files and repair common Windows errorsA dirhodium catalyst reported in 2017 showed how catalyst design can steer a reaction toward an exposed, unactivated tertiary C–H bond—even in complex molecules containing other potentially reactive sites. The result demonstrated selective chemistry in the laboratory, not a general-purpose or manufacturing-ready platform.
What did the catalyst do?
Carbon–hydrogen bonds are abundant in organic molecules, and a single molecule may contain many similar sites. Choosing one bond to modify without relying on its inherent reactivity, a directing group, or an intramolecular setup is a longstanding challenge in synthesis.
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In a Nature paper published on 20 November 2017, Kuangbiao Liao and colleagues at Emory University reported a dirhodium catalyst, Rh2(S-TCPTAD)4, that favored the most accessible non-activated tertiary C–H bond in the substrates they tested. “Tertiary” means the carbon bearing the hydrogen is attached to three other carbon atoms; “non-activated” here means the C–H bond is not next to a functional group. Read the paper’s abstract in Nature.
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The reaction used a donor–acceptor carbene to functionalize alkanes. The reported outcome therefore combined two kinds of control: site selectivity, or which C–H bond reacted, and stereoselectivity, or which three-dimensional arrangement of the new product formed.
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How could catalyst shape influence site selection?
Chemistry World described the catalyst as bowl-shaped, with its ligands modified from an earlier dirhodium catalyst that targeted accessible secondary C–H bonds. The proposed steric effect is straightforward: a crowded catalyst environment can make buried bonds harder to reach, favoring a more exposed site.
The account also describes modeling that suggested the ligands rearrange when the carbene binds to rhodium, leaving one face of the carbene more available for forming a new bond. This is the authors’ proposed explanation for the tested reaction, not a universal mechanism for dirhodium catalysts. Chemistry World’s report explains the proposed design.
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What results and substrates were reported?
Chemistry World reported maximum values of 93% yield and 92% enantiomeric excess. These are best reported results in the account, not typical outcomes or guarantees for every substrate; the account does not identify a named substrate and condition set for each maximum.
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Scan for outdated or missing drivers - takes under a minuteDriver Scan →Repair Windows errors before they cause bigger problemsFix Now →Fix the driver behind crashes, sound loss and screen glitchesFind Drivers →The authors tested complex molecules, including steroids and a vitamin E derivative. Chemistry World also described a lengthy hydrocarbon and cholesterol derivatives. In the reported examples, the catalyst selected accessible unactivated tertiary C–H sites even when more reactive allylic or benzylic C–H bonds were present. That is evidence of a late-stage functionalization proof of concept: a complex molecule can be modified at a chosen site without first simplifying its structure.
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What does the result establish—and what does it not?
- It establishes: catalyst choice can shift the preferred site class. The 2017 catalyst favored accessible tertiary sites, while the group’s earlier catalyst targeted accessible secondary C–H bonds.
- It demonstrates: site selection and stereochemical control can be achieved together in the tested carbene-transfer reactions.
- It does not establish: that every exposed tertiary C–H bond will react selectively, that all substrates will approach the reported maximum yield or enantiomeric excess, or that the method is broadly adopted in industrial synthesis.
The paper presents wider application as a goal for future catalyst design. Its authors wrote: “We hope that this work will inspire the design of even more sophisticated catalysts, such that catalyst-controlled C–H functionalization becomes a broadly applied strategy for the synthesis of complex molecules.”
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Why is this useful to synthesis research?
Many approaches to C–H functionalization depend on a substrate’s own reactivity, a directing group, or an intramolecular arrangement to favor one site. This study illustrates a different design strategy: tune the catalyst to recognize accessibility and steer a transformation among sites that might otherwise be difficult to distinguish.
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For comparing such methods, the meaningful questions are which class of C–H bond is targeted, what drives site selection, whether stereochemistry is controlled, which substrate types were actually demonstrated, and what yield and enantiomeric excess were achieved for each individual substrate. The two reported headline maxima alone cannot answer those substrate-by-substrate questions.
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Repair common Windows errors and clear accumulated junk for a smoother, more stable PC - no reinstall needed.Free scan · no reinstallSources: Liao et al., “Site-selective and stereoselective functionalization of non-activated tertiary C–H bonds,” Nature 551, 609–613 (published 20 November 2017); Melissae Fellet, Chemistry World (24 November 2017).
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