Nickel(0)‐Catalyzed <i>N</i>‐Allylation of Amides and <i>p</i>‐Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

Azizi, Mohamed Salah; Edder, Youssef; Karim, Abdallah; Sauthier, Mathieu

doi:10.1002/ejoc.201600500

Cited by 38 publications

(31 citation statements)

References 72 publications

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“…N-(3-Dimethylaminopropyl) methacrylamide (DAP-MAA), and 3-(methacryloyloxy) propyltrimethoxysilane (MPS) (CR for these chemical reagents, from Chengdu Huaxia Chemical Reagent Factory, Sichuan, China). Methylethylene sulte (MES), monomers MMPES and DMBSA were prepared according to the literature [38][39][40] (for details for MMPES and DMBSA see ESI †).…”

Section: Methodsmentioning

confidence: 99%

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

Gou

Huang

et al. 2019

RSC Adv.

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Section: Methodsmentioning

confidence: 99%

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

Gou

Huang

et al. 2019

RSC Adv.

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“…For example, we are exploring the organometallicc hemistry of nickel, [10][11][12][13][14] which has undergone ar enaissance in recent years. [15][16][17][18][19][20][21] Our focus has been the structure and reactivityo fn ickel p-complexes, which have been reported in aw ide range of catalytic processes, including the coupling of CO 2 and ethylene, [5,[22][23][24][25][26][27][28][29][30][31][32] intermolecular Tischenkoc oupling, [33][34][35] benzoxasilole synthesis, [36,37] the aldol reaction, [38] allylic alkylation, [39] allylic amination, [40] allylic amidation, [41] epoxide functionalization, [42] and Suzuki-Miyaura coupling. [43] Nickel p-complexes of heteroarenes have also been identified as key intermediates in nickel-catalysed catalystt ransfer polycondensation to form polythiophenes.…”

Section: Introductionmentioning

confidence: 99%

The Importance of Ligand‐Induced Backdonation in the Stabilization of Square Planar d¹⁰ Nickel π‐Complexes

Desnoyer

Behyan

et al. 2019

Chemistry A European J

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The electronic nature of Ni π‐complexes is underexplored even though these complexes have been widely postulated as intermediates in organometallic chemistry. Herein, the geometric and electronic structure of a series of nickel π‐complexes, Ni(dtbpe)(X) (dtbpe=1,2‐bis(di‐tert‐butyl)phosphinoethane; X=alkene or carbonyl containing π‐ligands), is probed using a combination of 31P NMR, Ni K‐edge XAS, Ni Kβ XES, and DFT calculations. These complexes are best described as square planar d10 complexes with π‐backbonding acting as the dominant contributor to M−L bonding to the π‐ligand. The degree of backbonding correlates with 2JPP from NMR and the energy of the Ni 1s→4pz pre‐edge in the Ni K‐edge XAS data, and is determined by the energy of the π*ip ligand acceptor orbital. Thus, unactivated olefinic ligands tend to be poor π‐acids whereas ketones, aldehydes, and esters allow for greater backbonding. However, backbonding is still significant even in cases in which metal contributions are minor. In such cases, backbonding is dominated by charge donation from the diphosphine, which allows for strong backdonation, although the metal centre retains a formal d10 electronic configuration. This ligand‐induced backbonding can be formally described as a 3‐centre‐4‐electron (3c‐4e) interaction, in which the nickel centre mediates charge transfer from the phosphine σ‐donors to the π*ip ligand acceptor orbital. The implications of this bonding motif are described with respect to both structure and reactivity.

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“…The allylation of α‐branched aldehydes would involve a [(dppf)Ni 0 (allyl aclohol)] complex A , which forms the pentacoordinated complex B through an oxidative addition step (Scheme ) . The hydroxy ligand acts as a base and reacts with the aldehyde to generate the enolate.…”

Section: Methodsmentioning

confidence: 99%

Nickel‐Catalyzed α‐Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols

et al. 2017

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An additive‐free nickel‐catalyzed α‐allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol % of in situ formed nickel complex in methanol, and water is the sole by‐product of the reaction. The experimental conditions allow the conversion of various α‐branched aldehydes and α,β‐unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/α‐allylation reaction.

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Nickel(0)‐Catalyzed N‐Allylation of Amides and p‐Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

Cited by 38 publications

References 72 publications

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

The Importance of Ligand‐Induced Backdonation in the Stabilization of Square Planar d¹⁰ Nickel π‐Complexes

Nickel‐Catalyzed α‐Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols

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Nickel(0)‐Catalyzed N‐Allylation of Amides and p‐Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

Cited by 38 publications

References 72 publications

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

The Importance of Ligand‐Induced Backdonation in the Stabilization of Square Planar d10 Nickel π‐Complexes

Nickel‐Catalyzed α‐Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols

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The Importance of Ligand‐Induced Backdonation in the Stabilization of Square Planar d¹⁰ Nickel π‐Complexes