ArticleAngewandte Chemie (International ed. in English)2021
Synthesis of Nitrile Bearing Acyclic Quaternary Centers through Co(III)-Catalyzed Sequential C-H Bond Addition to Dienes and N-Cyanosuccinimide.
Article in Angewandte Chemie (International ed. in English), 2021. 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, 6 citations in OpenAlex.
- C-H Activation and Sequential Addition to Dienes and Imines: Synthesis of Amines withACS catalysis · 2024Article
- Synthesis of α-Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Dienes and Isocyanates.Organic letters · 2024Article
- Three-component carboformylation: α-quaternary aldehyde synthesisChemical science · 2022Article
- An enzyme-mimic single Fe-NScience advances · 2022Article
- C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.Chemical Society reviews · 2022Review
- Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.Angewandte Chemie (International ed. in English) · 2022Article
- Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.Chemical science · 2021Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Herein we disclose a three-component strategy to access quaternary centers bearing nitriles by cobalt-catalyzed C-H bond activation and sequential addition to internally substituted 1,3-dienes and an electrophilic cyanating reagent with high regio and stereocontrol. 2-Aryl and alkyl monosubstituted dienes provide α-aryl and α-alkyl α-methyl-substituted nitriles, respectively. An even wider variety of functionality can be installed at the quaternary carbon by using 1,2-disubstituted dienes. The synthetic utility of the nitrile products was successfully demonstrated by various transformations, including conversions to γ-lactones and tetrazoles. The observed connectivity in the products along with studies with deuterium labeled reactants provide insight into the mechanism. Formation of a 7-membered cobaltacycle by C-H activation and migratory insertion of the diene is followed by β-hydride elimination and hydride reinsertion to give a 6-membered cobaltacycle that then reacts with the cyanating agent.
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Registered trials
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