ArticleScientific reports2016
Metal-Free C-H Alkyliminylation and Acylation of Alkenes with Secondary Amides.
Article in Scientific reports, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 79 citations in OpenAlex.
- One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors.Organic letters · 2023Article
- Mild and Expeditious Synthesis of Sulfenyl Enaminones of l-α-Amino Esters and Aryl/Alkyl Amines through NCS-Mediated Sulfenylation.ACS omega · 2021Article
- Direct alkylation of N,N-dialkyl benzamides with methyl sulfides under transition metal-free conditions.Communications chemistry · 2021Article
- A Novel Class of 7-Membered Heterocyclic Compounds.European journal of organic chemistry · 2020Article
- A redox-neutral synthesis of ketones by coupling of alkenes and amides.Nature communications · 2019Article
- Mild Reductive Functionalization of Amides intoChemistryOpen · 2017Article
- Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides under Mild Conditions.Organic letters · 2017Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Carbon-carbon bond formation by metal-free cross-coupling of two reactants with low reactivity represents a challenge in organic synthesis. Secondary amides and alkenes are two classes of bench-stable compounds. The low electrophilicity of the former and low nucleophilicity of the latter make the direct coupling of these two partners challenging yet highly desirable. We report herein an unprecedented intermolecular reaction of secondary amides with alkenes to afford α,β-unsaturated ketimines or enones, which are versatile intermediates for organic synthesis and are prevalent in bioactive compounds and functional materials. Our strategy relies on the chemoselective activation of the secondary amide with trifluoromethanesulfonic anhydride (Tf2O)/2-fluoropyridine to generate a highly reactive nitrilium intermediate, which reacts efficiently with alkenes. This metal-free synthesis is characterized by its mild reaction conditions, excellent functional group tolerance and chemoselectivity, allowing the preparation of multi-functionalized compounds without using protecting groups.
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Registered trials
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