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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
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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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Introduction
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Programmed selective sp2 C-O bond activation toward multiarylated benzenes.

Fei Zhao1, Yun-Fei Zhang, Jing Wen

  • 1Beijing National Laboratory of Molecular Sciences, College of Chemistry, Peking University, Beijing 100871, China.

Organic Letters
|June 25, 2013
PubMed
Summary
This summary is machine-generated.

Synthesize multiarylated benzenes efficiently using sequential cross-couplings of phloroglucinol derivatives. This method leverages palladium and nickel catalysis for selective C-O bond activation, enabling diverse product formation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Phloroglucinol derivatives are versatile building blocks in organic synthesis.
  • Efficient synthesis of multiarylated benzenes is crucial for various applications.
  • Selective activation of different carbon-oxygen (C-O) bonds remains a synthetic challenge.

Purpose of the Study:

  • To develop an efficient synthetic route for multiarylated benzenes.
  • To explore sequential cross-coupling reactions for C-O bond activation.
  • To achieve high selectivity in the synthesis of complex aromatic compounds.

Main Methods:

  • Utilized sequential cross-coupling reactions starting from phloroglucinol derivatives.
  • Employed palladium-catalyzed activation of C-OTs bonds.
  • Incorporated nickel-catalyzed activation of C-OC(O)NEt2 and C-OMe bonds.

Main Results:

  • Successfully synthesized a variety of important multiarylated benzenes.
  • Achieved high selectivity through rational design of reaction sequences.
  • Demonstrated the diverse reactivity of different C-O bonds under catalytic conditions.

Conclusions:

  • The developed sequential cross-coupling strategy provides an efficient method for synthesizing multiarylated benzenes.
  • The approach highlights the potential of selective C-O bond activation in complex molecule synthesis.
  • Rational design and catalyst choice are key to achieving high selectivity in these transformations.