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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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ortho–para-Directing Deactivators: Halogens01:24

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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7.0K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Surface-Controlled Mono/Diselective ortho C-H Bond Activation.

Qing Li1, Biao Yang1, Haiping Lin1

  • 1Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University , 199 Ren'ai Road, Suzhou, 215123, Jiangsu P. R. China.

Journal of the American Chemical Society
|February 9, 2016
PubMed
Summary

Researchers explored selective C-H bond activation on Au(111) and Ag(111) surfaces using phenol derivatives. Different surface selectivities were observed, offering new pathways for surface-assisted organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Surface Science
  • Catalysis

Background:

  • Selective C-H bond activation is a significant challenge in organic chemistry due to high bond dissociation enthalpies and poor reaction selectivity.
  • Phenol derivatives present complex substrates for C-H activation due to competing reaction pathways.

Purpose of the Study:

  • To investigate the selective ortho C-H functionalization and ortho-ortho couplings of phenol derivatives on Au(111) and Ag(111) surfaces.
  • To understand the influence of dehydrogenation and deoxygenation on reaction pathways and selectivity.

Main Methods:

  • Utilized Au(111) and Ag(111) metal surfaces as reaction platforms.
  • Employed scanning tunneling microscopy (STM) for surface imaging.
  • Applied density functional theory (DFT) for mechanistic calculations.
  • Used X-ray photoelectron spectroscopy (XPS) for surface analysis.

Main Results:

  • Observed diselective ortho C-H bond activation on Au(111) surfaces.
  • Observed monoselective ortho C-H bond activation on Ag(111) surfaces.
  • Demonstrated that the competition between dehydrogenation and deoxygenation dictates the reaction pathways.

Conclusions:

  • The study reveals distinct mono- and diselective C-H activation pathways on different metal surfaces.
  • Findings offer novel strategies for surface-assisted organic synthesis through controlled C-H bond activation.
  • The work provides fundamental insights into the mechanisms governing phenol derivative reactions on metal surfaces.