A comparison between (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions

Sudipta Modak; Suchibrata Borah; A.P. Prakasham; Mobin M. Shaikh; Raymond J. Butcher; Manoj Gangwar; Prasenjit Ghosh

doi:10.1016/j.ica.2019.119090

A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions

Sudipta Modak, Suchibrata Borah, A.P. Prakasham, Mobin M. Shaikh, Raymond J. Butcher, Manoj Gangwar, Prasenjit Ghosh (Corresponding author)

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

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Abstract

A comparison between (a/n-NHC)PdX₂(pyridine) (1b, 2b and 3) and (a/n-NHC)₂PdX₂ (X = halide) (1c, 2c and 4) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) and of the ubiquitous normal imidazole based N-heterocyclic carbenes (n-NHC) in Suzuki-Miyaura coupling reactions, revealed near comparable yields between the two (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ type complexes of the (a-NHC) and the (n-NHC) ligands. Indeed, the Density Functional Theory (DFT) studies performed on all of the (a/n-NHC)PdX₂(pyridine) (1b, 2b and 3) and (a/n-NHC)₂PdX₂ type complexes (1c, 2c and 4), indicated that as the latter (1c, 2c and 4), with two (a/n-NHC) ligands bound to the metal center were only marginally electron rich than the former (1b, 2b and 3), containing only one (a/n-NHC) ligand bound to metal center, no correlation of the electron richness of the metal centers with the catalysis yields was observed for these complexes. In this regard, the (a-NHC)PdI₂(pyridine) (1b and 2b) and the (a-NHC)₂PdI₂ (1c and 2c) type complexes of two new abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) have been synthesized and structurally characterized.

Original language	English
Article number	119090
Number of pages	9
Journal	Inorganica Chimica Acta
Volume	498
DOIs	https://doi.org/10.1016/j.ica.2019.119090
Publication status	Published - 1 Dec 2019
Externally published	Yes

Bibliographical note

Funding Information:
We thank the Department of Science and Technology (Grant No. SR/S1/IC-15/2011 ), New Delhi and Council of Scientific & Industrial Research ( CSIR ) { 01(2880)/17/EMR-II } New Delhi for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility at the Department of Chemistry, IIT Bombay, India for the crystallographic characterization data. SM and APP thank CSIR, New Delhi for research fellowship, SBB thanks IIT Bombay for the Institute Post-doctoral Fellowship.

Funding

We thank the Department of Science and Technology (Grant No. SR/S1/IC-15/2011 ), New Delhi and Council of Scientific & Industrial Research ( CSIR ) { 01(2880)/17/EMR-II } New Delhi for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility at the Department of Chemistry, IIT Bombay, India for the crystallographic characterization data. SM and APP thank CSIR, New Delhi for research fellowship, SBB thanks IIT Bombay for the Institute Post-doctoral Fellowship. We thank the Department of Science and Technology (Grant No. SR/S1/IC-15/2011), New Delhi and Council of Scientific & Industrial Research (CSIR) {01(2880)/17/EMR-II} New Delhi for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility at the Department of Chemistry, IIT Bombay, India for the crystallographic characterization data. SM and APP thank CSIR, New Delhi for research fellowship, SBB thanks IIT Bombay for the Institute Post-doctoral Fellowship.

Keywords

Abnormal (a-NHC)
Catalysis
Fused-bicyclic imidazo[1,2-a]pyridine
N-Heterocyclic carbene
Palladium
Suzuki coupling

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Modak, S., Borah, S., Prakasham, A. P., Shaikh, M. M., Butcher, R. J., Gangwar, M., & Ghosh, P. (2019). A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions. Inorganica Chimica Acta, 498, Article 119090. https://doi.org/10.1016/j.ica.2019.119090

Modak, Sudipta ; Borah, Suchibrata ; Prakasham, A.P. et al. / A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions. In: Inorganica Chimica Acta. 2019 ; Vol. 498.

@article{e94758dda7b44d6b993594774d54aef6,

title = "A comparison between (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions",

abstract = "A comparison between (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 (X = halide) (1c, 2c and 4) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) and of the ubiquitous normal imidazole based N-heterocyclic carbenes (n-NHC) in Suzuki-Miyaura coupling reactions, revealed near comparable yields between the two (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 type complexes of the (a-NHC) and the (n-NHC) ligands. Indeed, the Density Functional Theory (DFT) studies performed on all of the (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 type complexes (1c, 2c and 4), indicated that as the latter (1c, 2c and 4), with two (a/n-NHC) ligands bound to the metal center were only marginally electron rich than the former (1b, 2b and 3), containing only one (a/n-NHC) ligand bound to metal center, no correlation of the electron richness of the metal centers with the catalysis yields was observed for these complexes. In this regard, the (a-NHC)PdI2(pyridine) (1b and 2b) and the (a-NHC)2PdI2 (1c and 2c) type complexes of two new abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) have been synthesized and structurally characterized.",

keywords = "Abnormal (a-NHC), Catalysis, Fused-bicyclic imidazo[1,2-a]pyridine, N-Heterocyclic carbene, Palladium, Suzuki coupling",

author = "Sudipta Modak and Suchibrata Borah and A.P. Prakasham and Shaikh, {Mobin M.} and Butcher, {Raymond J.} and Manoj Gangwar and Prasenjit Ghosh",

note = "Funding Information: We thank the Department of Science and Technology (Grant No. SR/S1/IC-15/2011 ), New Delhi and Council of Scientific & Industrial Research ( CSIR ) { 01(2880)/17/EMR-II } New Delhi for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility at the Department of Chemistry, IIT Bombay, India for the crystallographic characterization data. SM and APP thank CSIR, New Delhi for research fellowship, SBB thanks IIT Bombay for the Institute Post-doctoral Fellowship. ",

year = "2019",

month = dec,

day = "1",

doi = "10.1016/j.ica.2019.119090",

language = "English",

volume = "498",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier B.V.",

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Modak, S, Borah, S, Prakasham, AP, Shaikh, MM, Butcher, RJ, Gangwar, M & Ghosh, P 2019, 'A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions', Inorganica Chimica Acta, vol. 498, 119090. https://doi.org/10.1016/j.ica.2019.119090

A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions. / Modak, Sudipta; Borah, Suchibrata; Prakasham, A.P. et al.
In: Inorganica Chimica Acta, Vol. 498, 119090, 01.12.2019.

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

TY - JOUR

T1 - A comparison between (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions

AU - Modak, Sudipta

AU - Borah, Suchibrata

AU - Prakasham, A.P.

AU - Shaikh, Mobin M.

AU - Butcher, Raymond J.

AU - Gangwar, Manoj

AU - Ghosh, Prasenjit

N1 - Funding Information: We thank the Department of Science and Technology (Grant No. SR/S1/IC-15/2011 ), New Delhi and Council of Scientific & Industrial Research ( CSIR ) { 01(2880)/17/EMR-II } New Delhi for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility at the Department of Chemistry, IIT Bombay, India for the crystallographic characterization data. SM and APP thank CSIR, New Delhi for research fellowship, SBB thanks IIT Bombay for the Institute Post-doctoral Fellowship.

PY - 2019/12/1

Y1 - 2019/12/1

N2 - A comparison between (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 (X = halide) (1c, 2c and 4) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) and of the ubiquitous normal imidazole based N-heterocyclic carbenes (n-NHC) in Suzuki-Miyaura coupling reactions, revealed near comparable yields between the two (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 type complexes of the (a-NHC) and the (n-NHC) ligands. Indeed, the Density Functional Theory (DFT) studies performed on all of the (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 type complexes (1c, 2c and 4), indicated that as the latter (1c, 2c and 4), with two (a/n-NHC) ligands bound to the metal center were only marginally electron rich than the former (1b, 2b and 3), containing only one (a/n-NHC) ligand bound to metal center, no correlation of the electron richness of the metal centers with the catalysis yields was observed for these complexes. In this regard, the (a-NHC)PdI2(pyridine) (1b and 2b) and the (a-NHC)2PdI2 (1c and 2c) type complexes of two new abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) have been synthesized and structurally characterized.

AB - A comparison between (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 (X = halide) (1c, 2c and 4) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) and of the ubiquitous normal imidazole based N-heterocyclic carbenes (n-NHC) in Suzuki-Miyaura coupling reactions, revealed near comparable yields between the two (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 type complexes of the (a-NHC) and the (n-NHC) ligands. Indeed, the Density Functional Theory (DFT) studies performed on all of the (a/n-NHC)PdX2(pyridine) (1b, 2b and 3) and (a/n-NHC)2PdX2 type complexes (1c, 2c and 4), indicated that as the latter (1c, 2c and 4), with two (a/n-NHC) ligands bound to the metal center were only marginally electron rich than the former (1b, 2b and 3), containing only one (a/n-NHC) ligand bound to metal center, no correlation of the electron richness of the metal centers with the catalysis yields was observed for these complexes. In this regard, the (a-NHC)PdI2(pyridine) (1b and 2b) and the (a-NHC)2PdI2 (1c and 2c) type complexes of two new abnormal fused-bicyclic imidazo[1,2-a]pyridine framework derived N-heterocyclic carbenes (a-NHC) have been synthesized and structurally characterized.

KW - Abnormal (a-NHC)

KW - Catalysis

KW - Fused-bicyclic imidazo[1,2-a]pyridine

KW - N-Heterocyclic carbene

KW - Palladium

KW - Suzuki coupling

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U2 - 10.1016/j.ica.2019.119090

DO - 10.1016/j.ica.2019.119090

M3 - Article

AN - SCOPUS:85072641653

SN - 0020-1693

VL - 498

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

M1 - 119090

ER -

Modak S, Borah S, Prakasham AP, Shaikh MM, Butcher RJ, Gangwar M et al. A comparison between (a/n-NHC)PdX₂(pyridine) and (a/n-NHC)₂PdX₂ (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions. Inorganica Chimica Acta. 2019 Dec 1;498:119090. doi: 10.1016/j.ica.2019.119090

A comparison between (a/n-NHC)PdX2(pyridine) and (a/n-NHC)2PdX2 (X = I, Cl) type complexes of abnormal fused-bicyclic imidazo[1,2-a]pyridine based N-heterocyclic carbene (a-NHC) and of normal imidazole based N-heterocyclic carbene (n-NHC) ligands in the Suzuki-Miyaura coupling reactions