Synthesis Of Biaryl Derivatives Research Articles

Synthesis of Biaryl Derivatives of Spirofurochromanone in Water and Their Anticancer Activity

Biaryl derivatives of spirofurochromanones have been synthesised from 4-bromophenyl derivatives of spirofurochromanones upon catalysis by Pd/C in water. Structures of the synthesised compounds are derived from IR, NMR and HRMS spectral data. The compounds have been tested for in vitro cytotoxicity supported by docking studies.

Palladium (II) complexes based on bidentate chiral Schiff base and amine ligands derived from (−)-myrtenal: Synthesis, characterization and catalytic activity in Suzuki reaction

(−)-Myrtenal 1 was reacted with N,N-dimethylethylenediamine and Na2SO4 in PhH to give Schiff base (HL, 2) in 98% yield. Imin 2 was reduced with NaBH4 in EtOH to give diamine (HL, 3) in 94% yield. Reactions of imine 2 and amine 3 with Li2PdCl4 in a 1:1 ratio in MeOH at room temperature provided the palladium chelates PdHLCl2 (4, 6) in 77 and 98% yields. Cyclopalladation of imine 2 using Pd(OAc)2 in PhH at 60 °C followed by treatment with LiCl furnished the chlorobridged dimeric cyclopalladated complex [μ-ClPdL]2 (5) in 61% yield. The proposed structures of new complexes 4–6 were confirmed by 1H, 13C{1H} and 2D NMR spectra. The X-ray analysis of PdCl2HL (4) also showed that the Schiff base acted as a bidentate ligand which could be coordinated to the Pd atom with the square planar geometry. Three new palladium complexes are used as catalysts for Suzuki cross-coupling reactions and exhibit high catalytic activity in the synthesis of biaryl derivatives.

Nickel(II) Schiff base complexes: Synthesis, characterization and catalytic activity in Kumada–Corriu cross-coupling reactions

The syntheses of ten new Ni(II) complexes 5a–5j with H2L tridentate (ONO) Schiff-base ligand (2-((2-oxybenzylidene)amino)phenolate) have been described and fully characterized by means of elemental analysis, FT–IR, electronic, 1H NMR and 13C NMR spectroscopy and single-crystal X-ray diffraction. In all [Ni(L)B] complexes (where B are imidazole, 4-benzylpyridine, 2-methyl-5-ethylpyridine, 3-hydroxymethylpyridine, 2-methylbenzimidazole, 2,6-dimethylpyridine, 4-methylpyridine, 2-isopropylbenzimidazole, 4-methylpiperidine or triphenylphosphine) the Schiff base completely deprotonates and coordinates to the metal ion as a dianionic tridentate ligand via the donor oxygens and nitrogen atoms. The coordination number of Ni(II) atoms is four with distorted square-planar stereochemistry. This is in a good agreement with the ligand field band position in their electronic spectra, as well as with the X-ray structure analysis for all complexes under study. Six selected complexes are used as catalysts for Kumada–Corriu cross-coupling reactions and exhibit a moderate to good catalytic activity in the synthesis of biaryl derivatives.

ChemInform Abstract: Synthesis of Biaryl Derivatives via a Magnetic Pd‐NPs‐Catalyzed One‐Pot Diazotization—Cross‐Coupling Reaction.

AbstractThe one‐pot diazotization‐cross coupling reaction of anilines (I) and arylboronic acids (II) affords the biaryls (III) in sufficient to high yields [with exception of (IIId)].

Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot ­Diazotization–Cross-Coupling Reaction

Correction to: Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot Diazotization–Cross-Coupling ReactionSynlett 2012; 23(16): 2393-2396DOI: 10.1055/s-0032-1317097

Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot Diazotization–Cross-Coupling Reaction

A magnetic Pd-NPs-catalyzed one-pot diazotization–cross-coupling reaction of anilines and arylboronic acids was developed. Biaryl derivatives were therefore synthesized in good to excellent yields. Through magnetic separation, the catalyst could be recovered and reused for five times. There were several obvious advantages such as broad applicability, high selectivity, simply experimental operation as well as the convenient preparation, high efficiency and reusability of catalyst.

A Novel One‐pot Synthesis of Biaryl Derivatives by Sequential Strategies via Suzuki Coupling/Knoevenagel Condensation in Aqueous Medium at Room Temperature

AbstractA novel one‐pot synthesis of biaryl derivatives has been developed starting from bromobenzaldehyde and phenylboronic acid in the presence of activated methylene compounds via sequential Suzuki coupling/Knoevenagel condensation in aqueous isopropanol medium at room temperature. Significantly, this strategy afforded a straightforward and efficient approach to construct original biaryls in which a new carbon double bond bound to activated moieties such as nitrile, ester and amide is formed from three simple substrates in a one‐pot procedure. Moreover, a wide scope of substrates could effectively participate in the process affording the target products in moderate to excellent yields.

ChemInform Abstract: Diversity‐Oriented Synthesis of Biaryl Derivatives Using Cross‐Enyne Metathesis, Diels—Alder Reaction, and Suzuki—Miyaura Cross‐Coupling as Key Steps.

AbstractStarting from alkynes (I) or (VIII), a three‐step sequence following conditions A), B) and C) leads to formation of unsymmetrical biaryl scaffolds.

ChemInform Abstract: Synthesis of Biaryl Derivatives by Using Ruthenium‐Mediated [2 + 2 + 2] Cyclotrimerization and Suzuki—Miyaura Cross‐Coupling as Key Steps.

AbstractThe title reaction produces m‐terphenyls of type (III).

Synthesis of Biaryl Derivatives by Using Ruthenium-Mediated [2+2+2] Cyclotrimerization and Suzuki-Miyaura Cross-Coupling as Key Steps

Functionalized biaryl derivatives have been prepared by applying [2+2+2] cyclotrimerization with the aid of Grubbs’ first-generation catalyst (G-I). The trimerized products were subjected to the Suzuki-Miyaura cross-coupling reaction sequence to generate highly functionalized biaryl derivatives.

Natural products as templates for bioactive compound libraries: synthesis of biaryl derivatives of (±)-vasicine

A reliable and high-yielding procedure for preparation of 7-aryl and 7-heteroaryl derivatives of (±)-vasicine in two steps from the naturally occurring material is described. This protocol broadens the chemical space for selective modifications of the vasicine tricyclic structure, thereby making it a valuable starting point for the development of novel compound libraries with potentially beneficial biological profiles.

ChemInform Abstract: Synthesis of Tiliacora Alcaloids. Part 3. Synthesis of Biaryl Derivatives Using the Ullmann Coupling.

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