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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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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...
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Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation.

Alexander Fanourakis1, Benjamin D Williams1, Kieran J Paterson1

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|June 28, 2021
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Researchers developed new ion-paired catalysts for enantioselective C-H amination. These catalysts, featuring chiral cations, achieve high selectivity in benzylic C-H amination, offering a dual role in catalysis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Enantioselective amination of C(sp3)-H bonds is crucial but challenging intermolecularly.
  • Existing catalysts like Rh2(esp)2 have limitations in achieving high enantioselectivity for this transformation.

Purpose of the Study:

  • To develop novel catalysts for highly enantioselective intermolecular C-H amination.
  • To explore the use of chiral cations in conjunction with Rh-based catalysts for enhanced selectivity and yield.

Main Methods:

  • Synthesis of anionic variants of Rh2(esp)2 catalyst.
  • Association of these variants with chiral cations derived from quaternized cinchona alkaloids.
  • Application of the resulting ion-paired catalysts in benzylic C-H amination reactions.

Main Results:

  • Achieved high levels of enantioselectivity in the benzylic C-H amination of substrates with pendant hydroxyl groups.
  • Observed improved product yields compared to the parent Rh2(esp)2 catalyst.
  • Identified dual role of the chiral cation, including axial ligation to the rhodium center.

Conclusions:

  • Chiral cations can effectively control enantioselectivity in challenging transition-metal-catalyzed transformations.
  • Ion-paired catalysts represent a promising strategy for advancing enantioselective C-H functionalization.
  • The developed methodology offers a powerful new tool for asymmetric synthesis.