NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes and the ligand effects on regioselectivity

Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hyd...

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Published inNature communications Vol. 13; no. 1; pp. 1890 - 10
Main Authors Wang, Xiao-Xu, Xu, Yuan-Tai, Zhang, Zhi-Lin, Lu, Xi, Fu, Yao
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 07.04.2022
Nature Publishing Group
Nature Portfolio
Subjects
119/118
140/131
140/58
639/638/403/933
639/638/403/934
639/638/77/888
Alkenes
Amines
Aminoquinolines
Bromides
Carboxylic acids
Catalysis
Catalysts
Chemical reactions
Computer applications
Coupling (molecular)
Cross coupling
Functional groups
Humanities and Social Sciences
Iodides
Ligands
multidisciplinary
Nickel
Nickel chloride
Nucleophiles
Organic chemistry
Reaction mechanisms
Regioselectivity
Science
Science (multidisciplinary)
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Abstract Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl 2 (PPh 3 ) 2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms. Difunctionalization of olefins is an ongoing and important focus of synthetic organic chemistry. Here the authors report a nickel-catalysed hydroalkylation of unactivated alkenes to obtain branched alkyl carboxylic acids or alkyl amines, using aminoquinoline and picolinamide as directing groups.
AbstractList Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl2(PPh3)2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms.Difunctionalization of olefins is an ongoing and important focus of synthetic organic chemistry. Here the authors report a nickel-catalysed hydroalkylation of unactivated alkenes to obtain branched alkyl carboxylic acids or alkyl amines, using aminoquinoline and picolinamide as directing groups.
Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl2(PPh3)2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms.Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl2(PPh3)2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms.
Difunctionalization of olefins is an ongoing and important focus of synthetic organic chemistry. Here the authors report a nickel-catalysed hydroalkylation of unactivated alkenes to obtain branched alkyl carboxylic acids or alkyl amines, using aminoquinoline and picolinamide as directing groups.
Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl 2 (PPh 3 ) 2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms. Difunctionalization of olefins is an ongoing and important focus of synthetic organic chemistry. Here the authors report a nickel-catalysed hydroalkylation of unactivated alkenes to obtain branched alkyl carboxylic acids or alkyl amines, using aminoquinoline and picolinamide as directing groups.
Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl (PPh ) as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms.
Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective hydroalkylation method applied to a broad range of unactivated alkenes remains challenging. Herein, we report a NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes to access β- or γ-branched alkyl carboxylic acids and β-, γ- or δ-branched alkyl amines. A broad range of alkyl iodides and bromides with different functional groups can be installed with excellent regiocontrol and availability for site-selective late-stage functionalization of biorelevant molecules. Under modified reaction conditions with NiCl 2 (PPh 3 ) 2 as the catalyst, migratory hydroalkylation takes place to provide β- (rather than γ-) branched products. The keys to success are the use of aminoquinoline and picolinamide as suitable directing groups and combined experimental and computational studies of ligand effects on the regioselectivity and detailed reaction mechanisms.
ArticleNumber 1890
Author Wang, Xiao-Xu
Fu, Yao
Lu, Xi
Zhang, Zhi-Lin
Xu, Yuan-Tai
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  fullname: Xu, Yuan-Tai
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  surname: Zhang
  fullname: Zhang, Zhi-Lin
  organization: Department of Hepatobiliary Surgery, The First Affiliated Hospital, Division of Life Sciences and Medicine, Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China
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  organization: Department of Hepatobiliary Surgery, The First Affiliated Hospital, Division of Life Sciences and Medicine, Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China
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  email: fuyao@ustc.edu.cn
  organization: Department of Hepatobiliary Surgery, The First Affiliated Hospital, Division of Life Sciences and Medicine, Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China, Institute of Energy, Hefei Comprehensive National Science Center
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35393419$$D View this record in MEDLINE/PubMed
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Snippet Alkene hydrocarbonation reactions have been developed to supplement traditional electrophile-nucleophile cross-coupling reactions. The branch-selective...
Difunctionalization of olefins is an ongoing and important focus of synthetic organic chemistry. Here the authors report a nickel-catalysed hydroalkylation of...
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StartPage 1890
SubjectTerms 119/118
140/131
140/58
639/638/403/933
639/638/403/934
639/638/77/888
Alkenes
Amines
Aminoquinolines
Bromides
Carboxylic acids
Catalysis
Catalysts
Chemical reactions
Computer applications
Coupling (molecular)
Cross coupling
Functional groups
Humanities and Social Sciences
Iodides
Ligands
multidisciplinary
Nickel
Nickel chloride
Nucleophiles
Organic chemistry
Reaction mechanisms
Regioselectivity
Science
Science (multidisciplinary)
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Title NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes and the ligand effects on regioselectivity
URI https://link.springer.com/article/10.1038/s41467-022-29554-4
https://www.ncbi.nlm.nih.gov/pubmed/35393419
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https://www.proquest.com/docview/2648897077
https://pubmed.ncbi.nlm.nih.gov/PMC8990077
https://doaj.org/article/62dd0b8e80ee4f2086265133e30f0c27
Volume 13
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