Synthesis of palladium complexes derived from amido linked N-heterocyclic carbenes and their use in Suzuki cross coupling reactions

Rohit Singh Chauhan; Suryakant Nagar; Sucheta Chatterjee; Dibakar Goswami; David B. Cordes; Alexandra M. Z. Slawin; Trupti Tawde

doi:10.1002/zaac.202100150

Synthesis of palladium complexes derived from amido linked N-heterocyclic carbenes and their use in Suzuki cross coupling reactions

Rohit Singh Chauhan, Suryakant Nagar, Sucheta Chatterjee, Dibakar Goswami, David B. Cordes, Alexandra M. Z. Slawin, Trupti Tawde

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

Abstract

Treatment of 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar=furylmethyl,phenylmethyl) with excess K₂CO₃ and [PdCl₂(L−L)] (L−L=2 PPh₃, dppf) afforded orange compounds of composition [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-2-ylidene)]₂Pd (Ar=furylmethyl; phenylmethyl). These complexes were characterized by NMR (¹H and ¹³C{1H} NMR), IR and micro-analysis data. Subsequently, the catalytic efficiency of these complexes for cross coupling reactions between 4-haloarenens (halo=Br, I) and phenylboronic acid was studied under different solvents (acetonitrile, THF and DMF), temperatures with different catalyst loadings. The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-2-ylidene)]₂Pd was established by single crystal X-ray diffraction analysis.

Original language	English
Pages (from-to)	1334-1341
Number of pages	9
Journal	Zeitschrift für Anorganische und Allgemeine Chemie
Volume	Early View
Early online date	7 Jun 2021
DOIs	https://doi.org/10.1002/zaac.202100150
Publication status	Published - 8 Jul 2021

Keywords

N-heterocyclic carbene
[PdCl2(P−P)]
NMR
Suzuki Cross coupling

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10.1002/zaac.202100150

Chauhan_2021_ZAAC_Synthesis-palladium-complexes_AAM
Copyright © 2021 Wiley-VCH GmbH. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/zaac.202100150
Accepted author manuscript, 568 KB

Rohit Singh Chauhan CCDC 2011024: Experimental Crystal Structure Determination
Cordes, D. B. (Creator), Cambridge Crystallographic Data Centre, 22 Jun 2020
DOI: 10.5517/ccdc.csd.cc25hmr2
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title = "Synthesis of palladium complexes derived from amido linked N-heterocyclic carbenes and their use in Suzuki cross coupling reactions",

abstract = "Treatment of 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar=furylmethyl,phenylmethyl) with excess K2CO3 and [PdCl2(L−L)] (L−L=2 PPh3, dppf) afforded orange compounds of composition [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-2-ylidene)]2Pd (Ar=furylmethyl; phenylmethyl). These complexes were characterized by NMR (1H and 13C{1H} NMR), IR and micro-analysis data. Subsequently, the catalytic efficiency of these complexes for cross coupling reactions between 4-haloarenens (halo=Br, I) and phenylboronic acid was studied under different solvents (acetonitrile, THF and DMF), temperatures with different catalyst loadings. The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-2-ylidene)]2Pd was established by single crystal X-ray diffraction analysis.",

keywords = "N-heterocyclic carbene, [PdCl2(P−P)], NMR, Suzuki Cross coupling",

author = "Chauhan, {Rohit Singh} and Suryakant Nagar and Sucheta Chatterjee and Dibakar Goswami and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Trupti Tawde",

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

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language = "English",

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pages = "1334--1341",

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T1 - Synthesis of palladium complexes derived from amido linked N-heterocyclic carbenes and their use in Suzuki cross coupling reactions

AU - Chauhan, Rohit Singh

AU - Nagar, Suryakant

AU - Chatterjee, Sucheta

AU - Goswami, Dibakar

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Tawde, Trupti

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

PY - 2021/7/8

Y1 - 2021/7/8

N2 - Treatment of 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar=furylmethyl,phenylmethyl) with excess K2CO3 and [PdCl2(L−L)] (L−L=2 PPh3, dppf) afforded orange compounds of composition [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-2-ylidene)]2Pd (Ar=furylmethyl; phenylmethyl). These complexes were characterized by NMR (1H and 13C{1H} NMR), IR and micro-analysis data. Subsequently, the catalytic efficiency of these complexes for cross coupling reactions between 4-haloarenens (halo=Br, I) and phenylboronic acid was studied under different solvents (acetonitrile, THF and DMF), temperatures with different catalyst loadings. The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-2-ylidene)]2Pd was established by single crystal X-ray diffraction analysis.

AB - Treatment of 1-(n-butyl)-3-N-(2-Ar)acetamido-1, 3-imidazolium chloride (Ar=furylmethyl,phenylmethyl) with excess K2CO3 and [PdCl2(L−L)] (L−L=2 PPh3, dppf) afforded orange compounds of composition [(1-(n-butyl)-3-N-(2-Ar)acetamido-1,3-imidazol-2-ylidene)]2Pd (Ar=furylmethyl; phenylmethyl). These complexes were characterized by NMR (1H and 13C{1H} NMR), IR and micro-analysis data. Subsequently, the catalytic efficiency of these complexes for cross coupling reactions between 4-haloarenens (halo=Br, I) and phenylboronic acid was studied under different solvents (acetonitrile, THF and DMF), temperatures with different catalyst loadings. The molecular structure of [(1-(n-butyl)-3-N-(2-furylmethyl)acetamido-1, 3-imidazol-2-ylidene)]2Pd was established by single crystal X-ray diffraction analysis.

KW - N-heterocyclic carbene

KW - [PdCl2(P−P)]

KW - NMR

KW - Suzuki Cross coupling

U2 - 10.1002/zaac.202100150

DO - 10.1002/zaac.202100150

M3 - Article

SN - 0044-2313

VL - Early View

SP - 1334

EP - 1341

JO - Zeitschrift für Anorganische und Allgemeine Chemie

JF - Zeitschrift für Anorganische und Allgemeine Chemie

ER -

Synthesis of palladium complexes derived from amido linked N-heterocyclic carbenes and their use in Suzuki cross coupling reactions

Abstract

Keywords

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Rohit Singh Chauhan CCDC 2011024: Experimental Crystal Structure Determination

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