ArticleJournal of the American Chemical Society2014
General allylic C-H alkylation with tertiary nucleophiles.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 107 citations in OpenAlex.
- General Light-Induced Pd-Catalyzed Allylic C-H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers.Journal of the American Chemical Society · 2025Article
- Excited-State Palladium-Catalyzed Radical Allylic Alkylation: Rapid Access to C2-Allyl Carbohydrates.ACS catalysis · 2025Article
- Article
- Efficient Palladium-Catalyzed Aerobic Oxidative Carbocyclization to Seven-Membered Heterocycles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Allylic C(spChemical science · 2020Article
- Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.Journal of the American Chemical Society · 2018Article
- Metal-free direct alkylation of unfunctionalized allylic/benzylic spChemical science · 2017Article
- Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.Angewandte Chemie (International ed. in English) · 2016Article
- N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.Journal of the American Chemical Society · 2014Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A general method for intermolecular allylic C-H alkylation of terminal olefins with tertiary nucleophiles has been accomplished employing palladium(II)/bis(sulfoxide) catalysis. Allylic C-H alkylation furnishes products in good yields (avg. 64%) with excellent regio- and stereoselectivity (>20:1 linear:branched, >20:1 E:Z). For the first time, the olefin scope encompasses unactivated aliphatic olefins as well as activated aromatic/heteroaromatic olefins and 1,4-dienes. The ease of appending allyl moieties onto complex scaffolds is leveraged to enable this mild and selective allylic C-H alkylation to rapidly diversify phenolic natural products. The tertiary nucleophile scope is broad and includes latent functionality for further elaboration (e.g., aliphatic alcohols, α,β-unsaturated esters). The opportunities to effect synthetic streamlining with such general C-H reactivity are illustrated in an allylic C-H alkylation/Diels-Alder reaction cascade: a reactive diene is generated via intermolecular allylic C-H alkylation and approximated to a dienophile contained within the tertiary nucleophile to furnish a common tricyclic core found in the class I galbulimima alkaloids.
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