ArticleNature2015
Rhodium-catalysed syn-carboamination of alkenes via a transient directing group.
Article in Nature, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 51 papers.
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Who cites it
51 citing papers in PubMed, 243 citations in OpenAlex.
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- Alkyne Carboamination with Imines Catalyzed by [pyOrganometallics · 2025Article
- Capturing Dichotomic Solvent Behavior in Solute-Solvent Reactions with Neural Network Potentials.Journal of chemical theory and computation · 2024Article
- Cu-Catalyzed Three-Component Alkene Carboamination: Mechanistic Insights and Rational Design to Overcome Limitations.Journal of the American Chemical Society · 2024Article
- Tuning light-driven oxidation of styrene inside water-soluble nanocages.Nature communications · 2024Article
- Photoexcitation of (diarylmethylene)amino benziodoxolones for alkylamination of styrene derivatives with carboxylic acids.Chemical science · 2024Article
- Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins.Organic letters · 2023Article
- Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts.Journal of the American Chemical Society · 2023Article
- Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins.Chemical science · 2023Article
- Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C-H functionalization.Nature communications · 2023Article
- Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction.Journal of the American Chemical Society · 2023Article
- Silver-Free C-H Activation: Strategic Approaches towards Realizing the Full Potential of C-H Activation in Sustainable Organic Synthesis.Angewandte Chemie (International ed. in English) · 2022Review
- Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters.Journal of the American Chemical Society · 2022Article
- C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.Chemical Society reviews · 2022Review
- Mapping Catalyst-Solvent Interplay in Competing Carboamination/Cyclopropanation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides.ACS catalysis · 2022Article
- Peptide-Catalyzed Stereoselective Conjugate Addition Reaction of Aldehydes to C-Substituted Maleimides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Ti-Catalyzed and -Mediated Oxidative Amination Reactions.Accounts of chemical research · 2021Article
- Rh(III)-Catalyzed Three-ComponentACS catalysis · 2021Article
- Copper-Catalyzed Three-Component Alkene Carbofunctionalization: C-N, C-O, and C-C Bond Formation from a Single Reaction Platform.Organic letters · 2021Article
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Authors and funding
2 authors at 1 institution in 1 country.
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Abstract
Alkenes are the most ubiquitous prochiral functional groups--those that can be converted from achiral to chiral in a single step--that are accessible to synthetic chemists. For this reason, difunctionalization reactions of alkenes (whereby two functional groups are added to the same double bond) are particularly important, as they can be used to produce highly complex molecular architectures. Stereoselective oxidation reactions, including dihydroxylation, aminohydroxylation and halogenation, are well established methods for functionalizing alkenes. However, the intermolecular incorporation of both carbon- and nitrogen-based functionalities stereoselectively across an alkene has not been reported. Here we describe the rhodium-catalysed carboamination of alkenes at the same (syn) face of a double bond, initiated by a carbon-hydrogen activation event that uses enoxyphthalimides as the source of both the carbon and the nitrogen functionalities. The reaction methodology allows for the intermolecular, stereospecific formation of one carbon-carbon and one carbon-nitrogen bond across an alkene, which is, to our knowledge, unprecedented. The reaction design involves the in situ generation of a bidentate directing group and the use of a new cyclopentadienyl ligand to control the reactivity of rhodium. The results provide a new way of synthesizing functionalized alkenes, and should lead to the convergent and stereoselective assembly of amine-containing acyclic molecules.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.