Copper hydride catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes

Abstract: Benzimidazoles are among the most important building blocks in pharmaceuticals, natural products, and functional materials. Although high demand for benzimidazole moieties in pharmaceuticals and academia has led chemists to develop more efficient strategies, synthetic methods for the functionalization of benzimidazoles are still limited. Herein, a simple and mild protocol for the synthesis of benzimidazole derivatives by copper hydride catalyzed C-H functionalization of benzimidazoles with allenes was developed.
The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system. The new copper hydride catalytic mechanism contributes more possibilities to modern organic synthesis

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch
Notes
Universität Freiburg, Dissertation, 2021

Keyword
Benzimidazoles
Copper
Benzimidazolderivate
Allenderivate
Katalyse

Event
Veröffentlichung
(where)
Freiburg
(who)
Universität
(when)
2021
Creator

DOI
10.6094/UNIFR/219315
URN
urn:nbn:de:bsz:25-freidok-2193151
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
25.03.2025, 1:57 PM CET

Data provider

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Time of origin

  • 2021

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