Acid‐Catalyzed Carbene Transfer from Diazo Compounds: Carbocation versus Carbene as Key Intermediate

Abstract: An efficient mechanism for the acid‐catalyzed formal carbene transfer from diazo compounds to nucleophilic substrates is disclosed by DFT calculations. In sharp contrast to recent proposal via neutral carbene‐like intermediates, the new mechanism involves selective diazo C‐protonation to form catalytic electrophilic carbocations, thus enabling a broad choice of metal‐free acid catalysts and nucleophilic substrates.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Acid‐Catalyzed Carbene Transfer from Diazo Compounds: Carbocation versus Carbene as Key Intermediate ; volume:2022 ; number:17 ; year:2022 ; extent:4
European journal of organic chemistry ; 2022, Heft 17 (2022) (gesamt 4)

Creator
Qu, Zheng‐Wang
Zhu, Hui
Grimme, Stefan

DOI
10.1002/ejoc.202200408
URN
urn:nbn:de:101:1-2022050215310610109425
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:22 AM CEST

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Associated

  • Qu, Zheng‐Wang
  • Zhu, Hui
  • Grimme, Stefan

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