ArticleNature communications2021
Three-component radical homo Mannich reaction.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 64 citations in OpenAlex.
- Photocatalytic generation of amidine carbon radicals for aminodihydroquinoline synthesis.Nature communications · 2025Article
- Total Synthesis of (±)-3-Thiaglutamate.Tetrahedron letters · 2024Article
- Hf(OTf)Molecules (Basel, Switzerland) · 2022Article
- Site-Selective α-C-H Functionalization of Trialkylamines via Reversible Hydrogen Atom Transfer Catalysis.Journal of the American Chemical Society · 2021Article
- Late-StageJournal of the American Chemical Society · 2021Article
- Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations.Nature communications · 2021Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aliphatic amine, especially tertiary aliphatic amine, is one of the most popular functionalities found in pharmaceutical agents. The Mannich reaction is a classical and widely used transformation for the synthesis of β-amino-carbonyl products. Due to an ionic nature of the mechanism, the Mannich reaction can only use non-enolizable aldehydes as substrates, which significantly limits the further applications of this powerful approach. Here we show, by employing a radical process, we are able to utilize enolizable aldehydes as substrates and develop the three-component radical homo Mannich reaction for the streamlined synthesis of γ-amino-carbonyl compounds. The electrophilic radicals are generated from thiols via the desulfurization process facilitated by visible-light, and then add to the electron-rich double bonds of the in-situ formed enamines to provide the products in a single step. The broad scope, mild conditions, high functional group tolerance, and modularity of this metal-free approach for the synthesis of complex tertiary amine scaffolds will likely be of great utility to chemists in both academia and industry.
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Registered trials
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