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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‡
a   Department of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Deguang Liu‡
a   Department of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Zhen Li
a   Department 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
b   School of Plant Protection, Anhui Agricultural University, Hefei 230036, P. R. of China
,
Wan Nie 
a   Department of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China
c   Department of Computer Science, City University of Hong Kong, Hong Kong SAR, P. R. of China
,
Xi Lu  ∗
a   Department of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Yao Fu∗
a   Department of Applied Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, P. R. of China
› Author AffiliationsFinancial support was received from the National Science Foundation of Anhui Province (2208085J26 and 2208085QB36) and the China Postdoctoral Science Foundation (2023TQ0343)
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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

Supporting 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

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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