Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions

Chandan Singh; A.P. Prakasham; Manoj Kumar Gangwar; Prasenjit Ghosh

doi:10.1002/slct.201801667

Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions

Chandan Singh, A.P. Prakasham, Manoj Kumar Gangwar, Prasenjit Ghosh

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

10 Citations (Scopus)

Abstract

A binuclear fused 5-membered palladacycle (2) and a palladium complex of amido-functionalized N-heterocyclic carbene (6) successfully performed the C_sp2−C_sp type Hiyama coupling followed by cyclization giving the biologically important benzofuran compounds in a convenient time economic method involving one-pot tandem reaction between 2-iodophenol and triethoxysilylalkynes. The aromatic triethoxysilylalkyne substrates exhibited higher yields than the aliphatic triethoxysilylalkyne substrates for both of the palladium complexes 2 (ca. 19−48%) and 6 (ca. 11−34%). The binuclear fused 5-membered palladacycle (2) was readily synthesized by the nucleophilic addition of 2-amino-pyridine on the cis-{(2,4,6-(CH₃)₃C₆H₂)NC}₂PdCl₂ in good yield (ca. 74%) and the palladium complex of amido-functionalized N-heterocyclic carbene (6) was synthesized by transmetallation route from the silver complex (5) with (COD)PdCl₂ in CH₃CN under reflux condition in ca. 38% of yield.

Original language	English
Pages (from-to)	9361-9367
Number of pages	7
Journal	ChemistrySelect
Volume	3
Issue number	32
DOIs	https://doi.org/10.1002/slct.201801667
Publication status	Published - 31 Aug 2018
Externally published	Yes

Bibliographical note

Funding Information:
We thank the Department of Science and Technology (EMR/2014/000254), New Delhi, India, and Council of Scientific & Industrial Research (CSIR) {01(2880)/17/EMR-II} New Delhi, India, for financial support of this research. We gratefully acknowledge Single Crystal X-ray Diffraction Facility, Department of Chemistry, IIT Bombay, Mumbai, India, for the crystallographic characterization data. C.S., A.P.P. and M.K.G., thank CSIR, New Delhi, India, for research fellowships.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Funding

We thank the Department of Science and Technology (EMR/2014/000254), New Delhi, India, and Council of Scientific & Industrial Research (CSIR) {01(2880)/17/EMR-II} New Delhi, India, for financial support of this research. We gratefully acknowledge Single Crystal X-ray Diffraction Facility, Department of Chemistry, IIT Bombay, Mumbai, India, for the crystallographic characterization data. C.S., A.P.P. and M.K.G., thank CSIR, New Delhi, India, for research fellowships.

Keywords

5-membered palladacycle
amido functionalized N-heterocyclic carbene
Hiyama alkynylation/cyclization
homogeneous catalysis
palladium

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title = "Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions",

abstract = "A binuclear fused 5-membered palladacycle (2) and a palladium complex of amido-functionalized N-heterocyclic carbene (6) successfully performed the Csp2−Csp type Hiyama coupling followed by cyclization giving the biologically important benzofuran compounds in a convenient time economic method involving one-pot tandem reaction between 2-iodophenol and triethoxysilylalkynes. The aromatic triethoxysilylalkyne substrates exhibited higher yields than the aliphatic triethoxysilylalkyne substrates for both of the palladium complexes 2 (ca. 19−48%) and 6 (ca. 11−34%). The binuclear fused 5-membered palladacycle (2) was readily synthesized by the nucleophilic addition of 2-amino-pyridine on the cis-{(2,4,6-(CH3)3C6H2)NC}2PdCl2 in good yield (ca. 74%) and the palladium complex of amido-functionalized N-heterocyclic carbene (6) was synthesized by transmetallation route from the silver complex (5) with (COD)PdCl2 in CH3CN under reflux condition in ca. 38% of yield.",

keywords = "5-membered palladacycle, amido functionalized N-heterocyclic carbene, Hiyama alkynylation/cyclization, homogeneous catalysis, palladium",

author = "Chandan Singh and A.P. Prakasham and Gangwar, {Manoj Kumar} and Prasenjit Ghosh",

note = "Funding Information: We thank the Department of Science and Technology (EMR/2014/000254), New Delhi, India, and Council of Scientific & Industrial Research (CSIR) {01(2880)/17/EMR-II} New Delhi, India, for financial support of this research. We gratefully acknowledge Single Crystal X-ray Diffraction Facility, Department of Chemistry, IIT Bombay, Mumbai, India, for the crystallographic characterization data. C.S., A.P.P. and M.K.G., thank CSIR, New Delhi, India, for research fellowships. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/slct.201801667",

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Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions. / Singh, Chandan; Prakasham, A.P.; Gangwar, Manoj Kumar et al.
In: ChemistrySelect, Vol. 3, No. 32, 31.08.2018, p. 9361-9367.

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

TY - JOUR

T1 - Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions

AU - Singh, Chandan

AU - Prakasham, A.P.

AU - Gangwar, Manoj Kumar

AU - Ghosh, Prasenjit

N1 - Funding Information: We thank the Department of Science and Technology (EMR/2014/000254), New Delhi, India, and Council of Scientific & Industrial Research (CSIR) {01(2880)/17/EMR-II} New Delhi, India, for financial support of this research. We gratefully acknowledge Single Crystal X-ray Diffraction Facility, Department of Chemistry, IIT Bombay, Mumbai, India, for the crystallographic characterization data. C.S., A.P.P. and M.K.G., thank CSIR, New Delhi, India, for research fellowships. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/8/31

Y1 - 2018/8/31

N2 - A binuclear fused 5-membered palladacycle (2) and a palladium complex of amido-functionalized N-heterocyclic carbene (6) successfully performed the Csp2−Csp type Hiyama coupling followed by cyclization giving the biologically important benzofuran compounds in a convenient time economic method involving one-pot tandem reaction between 2-iodophenol and triethoxysilylalkynes. The aromatic triethoxysilylalkyne substrates exhibited higher yields than the aliphatic triethoxysilylalkyne substrates for both of the palladium complexes 2 (ca. 19−48%) and 6 (ca. 11−34%). The binuclear fused 5-membered palladacycle (2) was readily synthesized by the nucleophilic addition of 2-amino-pyridine on the cis-{(2,4,6-(CH3)3C6H2)NC}2PdCl2 in good yield (ca. 74%) and the palladium complex of amido-functionalized N-heterocyclic carbene (6) was synthesized by transmetallation route from the silver complex (5) with (COD)PdCl2 in CH3CN under reflux condition in ca. 38% of yield.

AB - A binuclear fused 5-membered palladacycle (2) and a palladium complex of amido-functionalized N-heterocyclic carbene (6) successfully performed the Csp2−Csp type Hiyama coupling followed by cyclization giving the biologically important benzofuran compounds in a convenient time economic method involving one-pot tandem reaction between 2-iodophenol and triethoxysilylalkynes. The aromatic triethoxysilylalkyne substrates exhibited higher yields than the aliphatic triethoxysilylalkyne substrates for both of the palladium complexes 2 (ca. 19−48%) and 6 (ca. 11−34%). The binuclear fused 5-membered palladacycle (2) was readily synthesized by the nucleophilic addition of 2-amino-pyridine on the cis-{(2,4,6-(CH3)3C6H2)NC}2PdCl2 in good yield (ca. 74%) and the palladium complex of amido-functionalized N-heterocyclic carbene (6) was synthesized by transmetallation route from the silver complex (5) with (COD)PdCl2 in CH3CN under reflux condition in ca. 38% of yield.

KW - 5-membered palladacycle

KW - amido functionalized N-heterocyclic carbene

KW - Hiyama alkynylation/cyclization

KW - homogeneous catalysis

KW - palladium

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U2 - 10.1002/slct.201801667

DO - 10.1002/slct.201801667

M3 - Article

AN - SCOPUS:85052502774

SN - 2365-6549

VL - 3

SP - 9361

EP - 9367

JO - ChemistrySelect

JF - ChemistrySelect

IS - 32

ER -

Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions

Abstract

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Keywords

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