Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation

Qing-Wei Zhu; Deguang Liu; Zhen Li; Jia-Wang Wang; Wan Nie; Xi Lu; Yao Fu

doi:10.1055/a-2204-8921

Synthesis, Table of Contents

Synthesis 2024; 56(11): 1741-1748
DOI: 10.1055/a-2204-8921

paper

New Trends in Organic Synthesis from Chinese Chemists

Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation

Qing-Wei Zhu‡

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Deguang Liu‡

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Zhen Li

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Jia-Wang Wang

^bSchool of Plant Protection, Anhui Agricultural University, Hefei 230036, P. R. of China

,

Wan Nie

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

^cDepartment of Computer Science, City University of Hong Kong, Hong Kong SAR, P. R. of China

,

Xi Lu ∗

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

,

Yao Fu∗

^aDepartment of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China

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Abstract

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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 amines

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References

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