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

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^*

^*Corresponding author for this work

Department of Computer Science

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

2 Citations (Scopus)

Abstract

Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp³) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. 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 desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism. © 2023. Thieme. All rights reserved.

Original language	English
Pages (from-to)	1741-1748
Journal	Synthesis
Volume	56
Issue number	11
Online published	4 Dec 2023
DOIs	https://doi.org/10.1055/a-2204-8921
Publication status	Published - Jun 2024

Research Keywords

?-Branched amines
Alkene hydroalkylation
Alkenyl amides
Migratory hydroalkylation
Nickel catalysis
Phosphine ligand effects

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title = "Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation",

abstract = "Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. 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 desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism. {\textcopyright} 2023. Thieme. All rights reserved.",

keywords = "?-Branched amines, Alkene hydroalkylation, Alkenyl amides, Migratory hydroalkylation, Nickel catalysis, Phosphine ligand effects",

author = "Qing-Wei Zhu and Deguang Liu and Zhen Li and Jia-Wang Wang and Wan Nie and Xi Lu and Yao Fu",

year = "2024",

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doi = "10.1055/a-2204-8921",

language = "English",

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journal = "Synthesis",

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TY - JOUR

T1 - Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation

AU - Zhu, Qing-Wei

AU - Liu, Deguang

AU - Li, Zhen

AU - Wang, Jia-Wang

AU - Nie, Wan

AU - Lu, Xi

AU - Fu, Yao

PY - 2024/6

Y1 - 2024/6

N2 - Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. 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 desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism. © 2023. Thieme. All rights reserved.

AB - Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. 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 desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism. © 2023. Thieme. All rights reserved.

KW - ?-Branched amines

KW - Alkene hydroalkylation

KW - Alkenyl amides

KW - Migratory hydroalkylation

KW - Nickel catalysis

KW - Phosphine ligand effects

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U2 - 10.1055/a-2204-8921

DO - 10.1055/a-2204-8921

M3 - RGC 21 - Publication in refereed journal

SN - 0039-7881

VL - 56

SP - 1741

EP - 1748

JO - Synthesis

JF - Synthesis

IS - 11

ER -

Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation

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Research Keywords

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