ArticleBeilstein journal of organic chemistry2021
DABCO-promoted photocatalytic C-H functionalization of aldehydes.
Article in Beilstein journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 15 citations in OpenAlex.
- Curcumin-Enabled Metal-Free Photocatalytic Oxidation of Aryl- and Alkyl-methanamines to Imines Under Green Conditions.ChemSusChem · 2026Article
- Direct Acylation of Alkyl and Aryl Bromides via Nickel-Catalyzed Aldehyde C-H Functionalization.The Journal of organic chemistry · 2026Article
- Direct Synthesis of α‑Amino Ketones via Photochemical Nickel-Catalyzed Acyl-Aryl Cross-Coupling.ACS omega · 2025Article
- Redox-active molecules as organocatalysts for selective oxidative transformations - an unperceived organocatalysis field.Beilstein journal of organic chemistry · 2022Article
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5 authors at 1 institution in 1 country.
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Abstract
Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C-H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.
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