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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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Brook Rearrangement as Trigger for Dearomatization Reaction: Synthesis of Non-Aromatic N-Heterocycles.

Rajarshi Mondal1, Mohamed Agbaria1, Orit Cohen1

  • 1Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, Israel.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 6, 2023
PubMed
Summary

The [1,2]-Brook rearrangement enables dearomatization of aromatic N-heterocycles. This four-step method efficiently creates diverse, non-aromatic N-heterocycles with ambident reactivities.

Keywords:
Brook rearrangementdearomatizationheterocyclesmulticomponent reactionsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The [1,2]-Brook rearrangement is a valuable tool for molecular construction.
  • Dearomatization of aromatic N-heterocycles remains a synthetic challenge.

Purpose of the Study:

  • To showcase the utility of the [1,2]-Brook rearrangement in dearomatizing aromatic N-heterocycles.
  • To develop a versatile strategy for synthesizing diverse non-aromatic N-heterocycles.

Main Methods:

  • A four-step sequence involving lithiation, nucleophilic addition, [1,2]-Brook rearrangement, and dearomatization.
  • Exploration of various acyl silanes, halo-pyridines, and quinolines.

Main Results:

  • Successful dearomatization of aromatic N-heterocycles was achieved.
  • A diverse range of non-aromatic N-heterocycles with ambident reactivities were generated.
  • The methodology proved effective in constructing complex molecular architectures.

Conclusions:

  • The [1,2]-Brook rearrangement offers a powerful approach for the dearomatization of N-heterocycles.
  • This strategy provides access to valuable non-aromatic heterocyclic scaffolds.