ArticleACS catalysis2019
Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Catalytic Functionalization of Unactivated π-Bonds Enabled by Bidentate Directing Auxiliaries.Angewandte Chemie (International ed. in English) · 2026Review
- Elucidating Ligand-Dependent Selectivities in Pd-Catalyzed C-H Activations.Angewandte Chemie (International ed. in English) · 2025Article
- Palladium-Catalyzed Aerobic Alkene Arylboration: Coupling Aryl Boronic Acids, Alkenes, and Bis(pinacol)diboron.ACS catalysis · 2025Article
- Article
- Enantioselective Aminosilylation of Alkenes by Palladium/Ming-Phos-Catalyzed Tandem Narasaka-Heck/Silylation Reaction.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- 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
- Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides.Chemical science · 2022Article
- Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdAngewandte Chemie (International ed. in English) · 2022Article
- Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence.Chemical science · 2022Article
- Pd/Cu-Catalyzed amide-enabled selectivity-reversed borocarbonylation of unactivated alkenes.Chemical science · 2021Article
- Modular synthesis of non-conjugatedTetrahedron · 2021Article
- Mechanistic Studies of Pd(II)-CatalyzedACS catalysis · 2021Article
- Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives.Organic letters · 2021Article
- Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.Nature communications · 2020Article
- Controlling cyclization pathways in palladium(ii)-catalyzed intramolecular alkene hydro-functionalizationChemical science · 2020Article
- A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes.Angewandte Chemie (International ed. in English) · 2020Article
- Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.Israel journal of chemistry · 2020Article
- Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(spOrganic letters · 2020Article
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4 authors.
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Abstract
A substrate-directed enantioselective anti-carboboration reaction of alkenes has been developed, wherein a carbon-based nucleophile and a boron moiety are installed across the C=C bond through a 5-membered palladacycle intermediate. A preliminary result also shows it is possible to extend this reaction to alkenes that are more distal from the directing group and react via a 6-membered palladacycle. The reaction is promoted by a palladium(II) catalyst and a monodentate oxazoline ligand. A range of enantioenriched secondary alkylboronate products were obtained with moderate to high enantioselectivity that could be further upgraded by recrystallization. This work represents an efficient method to synthesize versatile and valuable alkylboronate building blocks. Building on an earlier mechanistic proposal by Peng, He, and Chen, a revised model is proposed to account for the stereoconvergent nature of this transformation.
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