ArticleAngewandte Chemie (International ed. in English)2020
A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 80 citations in OpenAlex.
- Catalytic Functionalization of Unactivated π-Bonds Enabled by Bidentate Directing Auxiliaries.Angewandte Chemie (International ed. in English) · 2026Review
- Ni/NHC-catalyzed C5-H alkylation and alkenylation of challenging furan(thiophene)-2-carboxaldehydes enabled by recyclable imine protecting group.Communications chemistry · 2025Article
- Palladium-catalyzed redox diversified entry to axially chiral styrenesChemical science · 2025Article
- Formate-Mediated C-C Coupling of Aryl/Vinyl Halides and Triflates: Carbonyl Arylation and Reductive Cross-Coupling.ACS catalysis · 2025Article
- N,N- and N,O-Bidentate-Chelation-Assisted Alkenyl C-H Functionalization.Molecules (Basel, Switzerland) · 2025Review
- Ligand Relay Catalysis Enables Asymmetric Migratory Hydroarylation for the Concise Synthesis of Chiral α-(Hetero)Aryl-Substituted Amines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification.Angewandte Chemie (International ed. in English) · 2023Article
- Extended Single-Electron Transfer Model and Dynamically Associated Energy Transfer Event in a Dual-Functional Catalyst System.JACS Au · 2023Article
- Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons.Nature communications · 2022Article
- A theoretical study based on DFT calculations on the different influence of functional groups on the C-H activation processRSC advances · 2022Article
- PdAngewandte Chemie (International ed. in English) · 2022Article
- Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis.Chemical science · 2021Article
- A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.Journal of the American Chemical Society · 2021Article
- NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines.Nature communications · 2021Article
- Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary.Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Metal-coordinating directing groups have seen extensive use in the field of transition-metal-catalyzed alkene functionalization; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in asymmetric organocatalysis, where reactions rely on reversible covalent interactions between an organic substrate and a chiral mediator, we have developed a transient-directing-group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of a commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.
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Registered trials
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.