ArticleNature communications2019
Geminal group-directed olefinic C-H functionalization via four- to eight-membered exo-metallocycles.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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Who cites it
8 citing papers in PubMed, 68 citations in OpenAlex.
- Alcohol-Directed Carboamination of Conjugated Enynes.Angewandte Chemie (International ed. in English) · 2026Article
- Pd-Catalyzed C(spThe Journal of organic chemistry · 2024Article
- Selective C-H Activation of Unprotected Allylamines by Control of Catalyst Speciation.Chem catalysis · 2023Article
- Hydrogen-bond-acceptor ligands enable distal C(spNature · 2023Article
- Regio- and Stereoselective 1,2-Oxyhalogenation of Non-Conjugated Alkynes via Directed Nucleopalladation: Catalytic Access to Tetrasubstituted Alkenes.Angewandte Chemie (International ed. in English) · 2022Article
- PdAngewandte Chemie (International ed. in English) · 2022Article
- Highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect.Chemical science · 2022Article
- Palladium/norbornene-catalyzed distal alkenyl C-H arylation and alkylation of cis-olefins.Tetrahedron · 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
Great efforts have been made in the activation of a C(alkenyl)-H bond vicinal to the directing group to proceed via five- or six-membered endo-metallocycles. In stark contrast, functionalization of a C(alkenyl)-H bond geminal to the directing group via exo-metallocycle pathway continued to be elusive. Here we report the selective transformation of an olefinic C-H bond that is geminal to the directing group bearing valuable hydroxyl, carbamate or amide into a C-C bond, which proceeds through four- to eight-membered exo-palladacycles. Compared to the reported mechanisms proceeding only through six-membered exo-palladacycles via N,N-bidentate chelation, our weak and O-monodentate chelation-assisted C(alkenyl)-H activations tolerate longer or shorter distances between the olefinic C-H bonds and the coordinating groups, allowing for the functionalizations of many olefinic C-H bonds in alkenyl alcohols, carbamates and amides. The synthetic applicability has been demonstrated by the preparative scale and late-stage C-H functionalization of steroid and ricinoleate derivatives.
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Registered trials
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