ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- The Genuine Carbene Conundrum.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Further Mechanistic Investigations into the Blue Light-Driven O-H Functionalization of Alcohols by Aryldiazoacetates.The Journal of organic chemistry · 2025Article
- Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions.ACS central science · 2025Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
5 authors.
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Abstract
The formal alkylation reaction of OH groups with diazoalkanes under catalyst-free reaction conditions finds broad application in organic synthesis. However, even today, this reaction is mainly limited to the use of diazomethane as reaction partner. In this combined experimental and theoretical study, we aim at a fundamental understanding of the reaction of diazoalkanes with alcohols to make this transformation amenable to a generalized approach towards formal alkylation reactions of alcohols with diazoalkanes. Experimental and theoretical studies suggest a direct proton transfer only in exceptional cases. In a more general setting, such O-H functionalization proceed both under dark and photochemical conditions via a key hydrogen-bonded singlet carbene intermediate that undergoes a protonation-addition mechanism. We conclude with applications of this approach in O-H functionalization reactions of alcohols, including simple fluorinated, halogenated and aliphatic alcohols and showcase functional-group tolerance of this method in the reaction of biologically active and pharmaceutically relevant alcohols.
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