1. Binuclear Fused 5-membered Palladacycle and Palladium Complex of Amido-Functionalized N-heterocyclic Carbene Precatalysts for the One-Pot Tandem Hiyama Alkynylation/Cyclization Reactions
- Author
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Chandan Singh, A. P. Prakasham, Prasenjit Ghosh, Manoj Kumar Gangwar, and Supramolecular Chemistry & Catalysis
- Subjects
ARYL HALIDES ,C-H ACTIVATION ,amido functionalized N-heterocyclic carbene ,chemistry.chemical_element ,ARYLBORONIC ACIDS ,Homogeneous catalysis ,010402 general chemistry ,01 natural sciences ,MIXED AQUEOUS-MEDIUM ,chemistry.chemical_compound ,BENZOFURAN DERIVATIVES ,Polymer chemistry ,CASCADE REACTIONS ,Hiyama alkynylation/cyclization ,Tandem ,010405 organic chemistry ,ORGANIC-SYNTHESIS ,General Chemistry ,palladium ,homogeneous catalysis ,0104 chemical sciences ,chemistry ,Alkynylation ,CATALYZED SUZUKI-MIYAURA ,5-membered palladacycle ,ARYLATION REACTIONS ,Carbene ,Palladium - 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)(3)C6H2)NC}(2)PdCl2 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. more...
- Published
- 2018
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