One-pot tandem hiyama alkynylation/cyclizations by palladium(II) acyclic diaminocarbene (ADC) complexes yielding biologically relevant benzofuran scaffolds

Chandan Singh, A. P. Prakasham, Manoj Kumar Gangwar, Raymond J. Butcher, Prasenjit Ghosh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A series of palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R1NH)(R2)methylidene]- PdCl2(CNR1) [R1 = 2, 4, 6-(CH3)3C6H2: R2 = NC5 H10 (2); NC4H8 (3); NC4H8O (4)] were used not only to perform the Csp2-Csp Hiyama coupling between aryl iodide and triethoxysilylalkynes but also to subsequently carry out the one-pot tandem Hiyama alkynylation/cyclization reaction between 2- iodophenol and triethoxysilylalkynes, giving a convenient timeefficient access to the biologically relevant benzofuran compounds. The palladium ADC complexes (2-4) were conveniently synthesized by the nucleophilic addition of secondary amines, namely, piperidine, pyrrolidine, and morpholine on the cis-{(2, 4, 6-(CH3)3C6H2)NC}2PdCl2 in moderate yields (ca. 61-66%) .

Original languageEnglish
Pages (from-to)1740-1756
Number of pages17
JournalACS Omega
Volume3
Issue number2
DOIs
StatePublished - 9 Feb 2018
Externally publishedYes

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