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

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

10 Citaten (Scopus)

Samenvatting

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.

Originele taal-2Engels
Pagina's (van-tot)9361-9367
Aantal pagina's7
TijdschriftChemistrySelect
Volume3
Nummer van het tijdschrift32
DOI's
StatusGepubliceerd - 31 aug. 2018
Extern gepubliceerdJa

Bibliografische nota

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

Financiering

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.

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