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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.3K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.3K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.7K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.3K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

20.6K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Bacterial cytochrome P450 for oxidative halogenated biaryl coupling.

Vanisa Petriti1, Katie Nolan2, Wenqiang Xu1

  • 1Department of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610 USA.

ACS Catalysis
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Summary

Marine-derived cytochrome P450 enzyme Bmp7 catalyzes halogenated biaryl formation. This biocatalyst enables greener synthesis of valuable biaryl compounds, expanding enzymatic capabilities for pharmaceuticals and materials.

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Area of Science:

  • Biocatalysis and enzyme engineering
  • Organic synthesis and medicinal chemistry

Background:

  • Biaryl motifs are crucial in pharmaceuticals, agrochemicals, and materials.
  • Traditional biaryl synthesis methods are often inefficient and unsustainable.
  • Biocatalytic approaches for halogenated biaryl coupling are underdeveloped.

Purpose of the Study:

  • To functionally characterize the marine-derived cytochrome P450 enzyme Bmp7.
  • To explore Bmp7's capability in catalyzing halogenated biaryl formation.
  • To elucidate the mechanism of Bmp7-catalyzed coupling reactions.

Main Methods:

  • Recombinant expression and characterization of Bmp7.
  • Substrate screening using a library of halogenated phenols.
  • Product identification via LC-HRMS, HRMS/MS, GC-MS, and NMR.
  • Structural analysis using X-ray crystallography and DFT calculations.

Main Results:

  • Bmp7 efficiently catalyzes C-C homocoupling of halogenated phenols, forming ortho-ortho linked biaryls.
  • Bmp7 accepts a broad range of 17 halogenated phenols as substrates.
  • Bmp7 also mediates heterocoupling reactions, producing mixed biaryl products.
  • X-ray crystallography and DFT calculations suggest a single-radical mechanism.

Conclusions:

  • Bmp7 is a novel biocatalyst for synthesizing halogenated biaryls.
  • This study provides a foundation for enzyme engineering and biocatalytic applications.
  • Bmp7 offers a sustainable alternative to traditional biaryl synthesis methods.