Synthesis of Terphenyls

Adrio, Luis A.; Mı́guez, José Manuel; Hii, King Kuok

doi:10.1080/00304940903163632

Cited by 23 publications

(4 citation statements)

References 105 publications

(88 reference statements)

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“…An interesting extension of the above-mentioned applications would be the synthesis of chiral, non-racemic polyaromatic systems aimed at the synthesis of materials emitting circularly polarized light (CPL), which is of interest for many optoelectronic applications [16][17][18]. In general, two primary approaches to the preparation of terphenyl compounds can be distinguished: (i) the coupling of dihalobenzene derivatives with aryl metal nucleophiles [19][20][21][22] and (ii) the use of open-chain precursor molecules to form the aromatic rings by concerted or sequential benzannulation reactions [22][23][24]. In 1994, Zimmermann [25] reported a ring transformation reaction of triarylpyrylium salts with aryl acetaldehydes to obtain substituted carbocycles.…”

Section: Introductionmentioning

confidence: 99%

2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes

Bauer,

Hofmann,

Reggelin

2023

Molecules

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A rapid synthesis of chiral sulfoxide-functionalized meta-terphenyl derivatives by a 2,5-[C4+C2] ring transformation reaction of pyrylium salts with in situ generated enantiomerically pure α-sulfinylacetaldehydes is described in this paper. This synthetic method demonstrates, for the first time, the use of α-sulfinylacetaldehydes in a reaction sequence initiated by the nucleophilic attack of pyrylium salts by α-sulfinylcarbanions to generate chiral aromatic systems. The method presented shows a broad applicability starting with various methyl sulfoxides and a number of functionalized pyrylium salts, furnishing meta-terphenyls with complex substitution patterns from readily accessible starting compounds.

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Section: Introductionmentioning

confidence: 99%

2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes

Bauer,

Hofmann,

Reggelin

2023

Molecules

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“…The importance of terphenyl frameworks has stimulated the development of a fair amount of synthetic methodology in this area . For the case of m -terphenyls, the most commonly employed strategies (Scheme ) can be summarized as follows: (a) aryl–aryl bond formation involving transition-metal-catalyzed reactions; (b) reaction of 1,2,3-trihalobenzenes or 2-lithio-1,3-dihalobenzenes with an aryl Grignard reagent via aryne intermediates; (c) generation of the central benzene ring by cycloaddition reactions or Michael-cyclocondensation sequences; and (d) pseudomulticomponent reactions between 2-bromoacrylates and phenylacetylenes via a Sonogashira-cycloaddition mechanism …”

Section: Introductionmentioning

confidence: 99%

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

et al. 2018

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The three-component reaction between alkyl-or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-mterphenyl derivatives containing β-alkylaminoor β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

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“…Oxygenated terphenyls and their derivatives are naturally occurring compounds, and their synthesis required several steps via cross-coupling reactions. 16 The present method is an alternate approach for quickly accessing these molecules. The reaction of ylide with methyl propiolate and methyl 3bromopropiolate afforded expected regioisomers of biaryl phenols 3o (78%) and 3p (69%).…”

mentioning

confidence: 99%

“…Treatment of p -haloaryl ynones with ylide afforded oxygenated terphenyls in good yields ( 3m – 3n ). Oxygenated terphenyls and their derivatives are naturally occurring compounds, and their synthesis required several steps via cross-coupling reactions . The present method is an alternate approach for quickly accessing these molecules.…”

mentioning

confidence: 99%

Ru-Catalyzed Benzannulation of Vinyl Sulfoxonium Ylide with Electron-Deficient Alkynes and Alkenes

et al. 2022

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Herein, we report carbene-mediated benzannulation of vinyl sulfoxonium ylides with electron-deficient alkynes and alkenes to synthesize oxygenated arenes. This protocol features excellent regioselectivity, a broad substrate scope, and mild reaction conditions. Mechanistic studies revealed that the reaction proceeds through furan generation, cycloaddition, ring cleavage, and aromatization cascades. The synthesized arenes have been utilized in diverse product transformations and arene ring homologation.

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Synthesis of Terphenyls

Cited by 23 publications

References 105 publications

2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes

2,5-[C4+C2] Ringtransformation of Pyrylium Salts with α-Sulfinylacetaldehydes

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

Ru-Catalyzed Benzannulation of Vinyl Sulfoxonium Ylide with Electron-Deficient Alkynes and Alkenes

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