Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions

Suryakant Nagar; Sucheta Chatterjee; Dibakar Goswami; David B. Cordes; A.M.Z. Slawin; Rohit Singh Chauhan; Pradnya Prabhu

doi:10.1016/j.ica.2020.119446

Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions

Suryakant Nagar, Sucheta Chatterjee, Dibakar Goswami, David B. Cordes, A.M.Z. Slawin, Rohit Singh Chauhan, Pradnya Prabhu

Research output: Contribution to journal › Article › peer-review

Abstract

The refluxing of chloroacetamide derivatives with n-butyl imidazole resulted in their corresponding salt of composition 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar = furylmethyl (1a); phenylmethyl (1b)). The latter salt on treatment with DBU followed by the addition of chalcogen atom resulted into a compound [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)E] (Ar = furylmethyl; E = S (2a); Ar = phenylmthyl; E = Se (2b)). Similarly, the reaction of the imidazolium salts with, excess K₂CO₃ and NiCl₂·6H₂O yielded compounds [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)]₂Ni (Ar = furylmethyl (3a); phenylmethyl (3b)). The latter complexes have also been isolated by using Ni(II) phosphine precursors [NiCl₂(PP)] (PP = PPh₃, dppf). The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-3-ylidine)]₂Ni and [(1-(n-butyl)-3-N-(2-phenylmethyl)acetamido-1, 3-imidazol-3-ylidine)]₂Ni were established by single crystal X-ray diffraction analysis. The catalytic property of complex 3a and 3b for cross coupling reactions has been studied.

Original language	English
Article number	119446
Journal	Inorganica Chimica Acta
Volume	504
Early online date	18 Jan 2020
DOIs	https://doi.org/10.1016/j.ica.2020.119446
Publication status	Published - 1 May 2020

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Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions (dataset)
Nagar, S. (Creator), Chatterjee, S. (Creator), Goswami, D. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Chauhan, R. S. (Creator) & Prabhu, P. (Creator), Cambridge Crystallographic Data Centre, 2019
https://dx.doi.org/10.5517/ccdc.csd.cc22721g and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc22722h (show fewer)
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@article{a90eb134a0024fdf8e0d121effd8da45,

title = "Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions",

abstract = "The refluxing of chloroacetamide derivatives with n-butyl imidazole resulted in their corresponding salt of composition 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar = furylmethyl (1a); phenylmethyl (1b)). The latter salt on treatment with DBU followed by the addition of chalcogen atom resulted into a compound [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)E] (Ar = furylmethyl; E = S (2a); Ar = phenylmthyl; E = Se (2b)). Similarly, the reaction of the imidazolium salts with, excess K2CO3 and NiCl2·6H2O yielded compounds [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)]2Ni (Ar = furylmethyl (3a); phenylmethyl (3b)). The latter complexes have also been isolated by using Ni(II) phosphine precursors [NiCl2(PP)] (PP = PPh3, dppf). The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni and [(1-(n-butyl)-3-N-(2-phenylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni were established by single crystal X-ray diffraction analysis. The catalytic property of complex 3a and 3b for cross coupling reactions has been studied.",

author = "Suryakant Nagar and Sucheta Chatterjee and Dibakar Goswami and Cordes, {David B.} and A.M.Z. Slawin and Chauhan, {Rohit Singh} and Pradnya Prabhu",

note = "One of the authors (RSC) is grateful to DST for the financial support under the DST young scientist scheme YSS/2014/000797.",

year = "2020",

month = may,

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doi = "10.1016/j.ica.2020.119446",

language = "English",

volume = "504",

journal = "Inorganica Chimica Acta",

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T1 - Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions

AU - Nagar, Suryakant

AU - Chatterjee, Sucheta

AU - Goswami, Dibakar

AU - Cordes, David B.

AU - Slawin, A.M.Z.

AU - Chauhan, Rohit Singh

AU - Prabhu, Pradnya

N1 - One of the authors (RSC) is grateful to DST for the financial support under the DST young scientist scheme YSS/2014/000797.

PY - 2020/5/1

Y1 - 2020/5/1

N2 - The refluxing of chloroacetamide derivatives with n-butyl imidazole resulted in their corresponding salt of composition 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar = furylmethyl (1a); phenylmethyl (1b)). The latter salt on treatment with DBU followed by the addition of chalcogen atom resulted into a compound [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)E] (Ar = furylmethyl; E = S (2a); Ar = phenylmthyl; E = Se (2b)). Similarly, the reaction of the imidazolium salts with, excess K2CO3 and NiCl2·6H2O yielded compounds [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)]2Ni (Ar = furylmethyl (3a); phenylmethyl (3b)). The latter complexes have also been isolated by using Ni(II) phosphine precursors [NiCl2(PP)] (PP = PPh3, dppf). The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni and [(1-(n-butyl)-3-N-(2-phenylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni were established by single crystal X-ray diffraction analysis. The catalytic property of complex 3a and 3b for cross coupling reactions has been studied.

AB - The refluxing of chloroacetamide derivatives with n-butyl imidazole resulted in their corresponding salt of composition 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar = furylmethyl (1a); phenylmethyl (1b)). The latter salt on treatment with DBU followed by the addition of chalcogen atom resulted into a compound [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)E] (Ar = furylmethyl; E = S (2a); Ar = phenylmthyl; E = Se (2b)). Similarly, the reaction of the imidazolium salts with, excess K2CO3 and NiCl2·6H2O yielded compounds [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-3-ylidine)]2Ni (Ar = furylmethyl (3a); phenylmethyl (3b)). The latter complexes have also been isolated by using Ni(II) phosphine precursors [NiCl2(PP)] (PP = PPh3, dppf). The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni and [(1-(n-butyl)-3-N-(2-phenylmethyl)acetamido-1, 3-imidazol-3-ylidine)]2Ni were established by single crystal X-ray diffraction analysis. The catalytic property of complex 3a and 3b for cross coupling reactions has been studied.

U2 - 10.1016/j.ica.2020.119446

DO - 10.1016/j.ica.2020.119446

M3 - Article

SN - 0020-1693

VL - 504

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

M1 - 119446

ER -

Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions

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Reactivity of nickel metal precursors towards amido linked N-heterocyclic carbenes and their catalytic studies for cross coupling reactions (dataset)

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