Coupling Of Anhydrides Research Articles

Single-Step Synthesis of γ-Ketoacids through a Photoredox-Catalyzed Dual Decarboxylative Coupling of α-Oxo Acids and Maleic Anhydrides.

A photocatalytic methodology for the single step synthesis of γ-ketoacids from α-ketoacids has been developed. This method employs maleic anhydrides as traceless synthetic equivalents of acrylic acids, achieving a selective cross-coupling via a dual decarboxylative strategy, where molecular CO2 is released as the only waste byproduct. The method has also been expanded to incorporate a highly regioselective, 3-component coupling with various alcohols to access functionalized γ-ketoesters.

Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize α-amino ketones.

α-Amino ketones are important motifs in synthetic and medicinal chemistry. Efficient methods to directly access these motifs from feasible precursors are, however, limited. Herein, a visible-light mediated reductive cross-electrophile coupling of readily available imines and anhydrides was developed. Under mild reaction conditions, the umpolung reactivity of diverse imines engaged with anhydrides gives a variety of α-amino ketones with good yields and a broad functional group compatibility. Primary mechanistic studies revealed that this transformation might proceed through a radical-radical cross coupling pathway dominantly.

Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes

A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.

Electroreductive Coupling of Phthalic Anhydrides with α,β-Unsaturated Carbonyl Compounds: Synthesis of 1,4-Dihydroxynaphthalenes.

Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds in the presence of TMSCl and subsequent treatment with 1 M HCl gave 1,4-dihydroxynaphthalenes and 2-methyl-2,3-dihydronaphthalene-1,4-diones.

Reductive coupling of phthalic anhydrides with aliphatic ketones by low-valent titanium: Unusual two-to-one coupling for preparation of 3,3-disubstituted phthalides

The reductive coupling of phthalic anhydrides with acetone by Zn-TiCl4 in THF gave two-to-one and one-to-one coupled products. The coupled products were transformed to 3,3-diisopropyl-, 3-isopropylidene-, and 3-isopropylphthalides. In addition, the reductive coupling of phthalic anhydrides with acetonylacetone by Zn-TiCl4 in THF gave 3-spirocyclopentanylphtalides stereoselectively.

ChemInform Abstract: Ligand‐Free Palladium‐Catalyzed Aerobic Oxidative Coupling of Carboxylic Anhydrides with Arylboronic Acids.

We report a new, effective and environmentally friendly protocol for selective aerobic oxidative coupling of arylboronic acids with carboxylic anhydrides in the presence of ligand-free palladium catalyst. The aryl benzoates are obtained in good to excellent yields.

Ligand-free palladium-catalyzed aerobic oxidative coupling of carboxylic anhydrides with arylboronic acids.

We report a new, effective and environmentally friendly protocol for selective aerobic oxidative coupling of arylboronic acids with carboxylic anhydrides in the presence of ligand-free palladium catalyst. The aryl benzoates are obtained in good to excellent yields.

ChemInform Abstract: Palladium‐Catalyzed Decarboxylative Coupling of Isatoic Anhydrides with Arylboronic Acids.

AbstractMechanistic experiments using deuterium labeling prove that the O‐atom of the carboxyl group derives from dioxygen after splitting off the carbon dioxide.

Palladium-Catalyzed Decarboxylative Coupling of Isatoic Anhydrides with Arylboronic Acids

The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd(2)(dba)(3) and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.

Branch‐Selective Intermolecular Hydroacylation: Hydrogen‐Mediated Coupling of Anhydrides to Styrenes and Activated Olefins.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Branch‐Selective Intermolecular Hydroacylation: Hydrogen‐Mediated Coupling of Anhydrides to Styrenes and Activated Olefins

Branching out with hydrogen: Hydrogenation of symmetric or mixed carboxylic anhydrides in the presence of styrenes or activated olefins generates intermolecular hydroacylation products. The use of cationic rhodium catalysts ligated by triphenylarsine (Ph3As) results in the formation of branched coupling products as single regioisomers in high yields (see scheme; cod=cycloocta-1,5-diene, ArF=3,5-(CF3)2C6H3).

Branch‐Selective Intermolecular Hydroacylation: Hydrogen‐Mediated Coupling of Anhydrides to Styrenes and Activated Olefins

Vorliebe für Verzweigungen: Die Hydrierung symmetrischer oder gemischter Carbonsäureanhydride in Gegenwart von Styrolen oder aktivierten Olefinen ergibt die Produkte der intermolekularen Hydroacylierung. Mit kationischen Rhodium-Triphenylarsan-Katalysatoren entstehen die verzweigten Kupplungsprodukte regiospezifisch in hohen Ausbeuten (siehe Schema; cod=Cycloocta-1,5-dien, ArF=3,5-(CF3)2C6H3). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2006/z602377_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Synthesis of 4‐Substituted Bisnaphthalimides.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of 4-Substituted Bisnaphthalimides

The synthetic route to 4-substituted bisnaphthalimides consisting in reaction of 4-halonaphthalic anhydrides with a,w-diaminoalkanes followed by halogen substitution with dialkylamino group is more promising than imidating coupling of 4-dialkylaminonaphthalic anhydrides for it opens wider synthetic opportunities and ensures better yields of target products. Dihalosubstituted bis-naphthalimides can be prepared by N-alkylation of the corresponding naphthalimides with polymethylene dibromides under conditions of phase-transfer catalysis in the presence of tetraalkylammonium salts.

Nouvelle application des anhydrides N-carboxy aminoacides : synthese des 1,4-benzodiazepine-2,5-diones

A new synthetic method for 1,4-benzodiazepine-2,5-dione (BZD) was accomplished by the coupling of amino acid N-carboxy anhydrides (NCAs) with Boc-anthranilic acid, followed by the deprotection of Boc group and by the ring expansion.

ChemInform Abstract: Peptide Synthesis in Alcohol Solvents by the Mixed Anhydride Method Using Dimethylphosphinothioyl Chloride.

AbstractThe formation and coupling of dimethylphosphinothioic mixed anhydrides of protected amino acids such as (II) can be performed in alcohol or alcohol/water solvents.

ChemInform Abstract: Cobalt(II) Chloride Catalysed Coupling of Thiols and Anhydrides: A New and Efficient Synthesis of Thiol Esters.

Chemischer InformationsdienstVolume 17, Issue 50 Isocyclic Compounds ChemInform Abstract: Cobalt(II) Chloride Catalysed Coupling of Thiols and Anhydrides: A New and Efficient Synthesis of Thiol Esters. S. AHMAD, S. AHMADSearch for more papers by this authorJ. IQBAL, J. IQBALSearch for more papers by this author S. AHMAD, S. AHMADSearch for more papers by this authorJ. IQBAL, J. IQBALSearch for more papers by this author First published: December 16, 1986 https://doi.org/10.1002/chin.198650198Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume17, Issue50December 16, 1986 RelatedInformation

Cobalt(II) chloride catalysed coupling of thiols and anhydrides: A new and efficient synthesis of thiol esters

Cobalt(II) chloride in acetonitrile catalyses the coupling of anhydrides or acid chlorides with thiols to yield thiol esters in excellent yields.

Palladium mediated synthesis of conjugated E or Z enones and unsymmetrical divinyl ketones. one-pot preparation of isoegomaketone

The palladium (o) catalyzed coupling of acyl halides or anhydrides with alkenyl copper reagents furnishes α,β ethylenic ketones and α,β-α,β' diethylenic ketones in high yield. The substitution pattern of the alkenyl copper reagent, directly obtained by carbocupration of alkynes, is fully retained. Anhydrides of Z-ethylenic acids also retain their Z stereochemistry. β-halogeno-vinyl ketones react under the above conditions to afford α,β-γ,δ dienones. An efficient one-pot synthesis of Z or ε isoegomaketone is reported.