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

doi:10.1021/acsomega.7b01974

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

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

36 Citations (Scopus)

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 C_sp^2-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 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 language	English
Pages (from-to)	1740-1756
Number of pages	17
Journal	ACS Omega
Volume	3
Issue number	2
DOIs	https://doi.org/10.1021/acsomega.7b01974
Publication status	Published - 9 Feb 2018
Externally published	Yes

Bibliographical note

Funding Information:
We thank the Department of Science and Technology (EMR/ 2014/000254), 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 American Chemical Society.

Funding

We thank the Department of Science and Technology (EMR/ 2014/000254), 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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10.1021/acsomega.7b01974

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title = "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 = 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\%) .",

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

note = "Funding Information: We thank the Department of Science and Technology (EMR/ 2014/000254), 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 American Chemical Society.",

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AU - Singh, Chandan

AU - Prakasham, A.P.

AU - Gangwar, Manoj Kumar

AU - Butcher, Raymond J.

AU - Ghosh, Prasenjit

N1 - Funding Information: We thank the Department of Science and Technology (EMR/ 2014/000254), 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 American Chemical Society.

PY - 2018/2/9

Y1 - 2018/2/9

N2 - 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%) .

AB - 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%) .

UR - https://www.scopus.com/pages/publications/85042457448

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DO - 10.1021/acsomega.7b01974

M3 - Article

AN - SCOPUS:85042457448

SN - 2470-1343

VL - 3

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IS - 2

ER -

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

Abstract

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