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One-Pot Tandem Hiyama Alkynylation/Cyclizations by Palladium(II) Acyclic Diaminocarbene (ADC) Complexes Yielding Biologically Relevant Benzofuran Scaffolds.

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 = NC₅H₁₀ (2); NC₄H₈ (3); NC₄H₈O (4)] were used not only to perform the C_sp² -C_sp 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 time-efficient 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%).

SUBMITTER: Singh C

PROVIDER: S-EPMC6641338 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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One-Pot Tandem Hiyama Alkynylation/Cyclizations by Palladium(II) Acyclic Diaminocarbene (ADC) Complexes Yielding Biologically Relevant Benzofuran Scaffolds.

Singh Chandan C Prakasham A P AP Gangwar Manoj Kumar MK Butcher Raymond J RJ Ghosh Prasenjit P

ACS omega 20180209 2

A series of palladium acyclic diaminocarbene (ADC) complexes of the type cis-[(R1NH)(R2)methylidene]PdCl2(CNR1) [R1 = 2,4,6-(CH3)3C6H2: R2 = NC5H10 (2); NC4H8 (3); NC4H8O (4)] were used not only to perform the Csp2 -Csp Hiyama coupling between aryl iodide and tri ...[more]

PMID: 31458491

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