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Synthesis 2024; 56(11): 1741-1748
DOI: 10.1055/a-2204-8921
DOI: 10.1055/a-2204-8921
paper
New Trends in Organic Synthesis from Chinese Chemists
Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation
Financial support was received from the National Science Foundation of Anhui Province (2208085J26 and 2208085QB36) and the China Postdoctoral Science Foundation (2023TQ0343)
Abstract
Catalytic alkene hydroalkylation has provided to be an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation followed by cross-coupling. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine-catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver the desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.
Key words
alkene hydroalkylation - nickel catalysis - phosphine ligand effects - migratory hydroalkylation - alkenyl amides - α-branched aminesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2204-8921.
- Supporting Information
Publication History
Received: 12 October 2023
Accepted after revision: 06 November 2023
Accepted Manuscript online:
06 November 2023
Article published online:
04 December 2023
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