Palladium-Catalyzed Carbonylative Cross-Coupling Research Articles

Palladium-Catalyzed Carbonylative Cross-Coupling of Difluoroalkyl Halides with Alkylboranes under 1 atm of CO.

A palladium catalyzed carbonylative cross-coupling of difluoroalkyl halides with alkyl-9-BBN under 1 atm of CO has been developed. The reaction shows broad substrate scope and high functional group tolerance, even toward complex pharmaceuticals, providing a general and straightforward method to access alkyldifluoroalkyl ketones. Preliminary mechanistic studies reveal that a radical pathway is involved in the reaction.

Palladium/aluminium-cocatalyzed carbonylative synthesis of 2-chloroethyl benzoates from epoxides and aryl iodides

A new straightforward and efficient procedure for the palladium/aluminium-cocatalyzed carbonylative synthesis of 2-chloroethyl benzoates from epoxides and aryl iodides has been developed. By using TFBen (benzene-1,3,5-triyl triformate) as the CO source and LiCl as the chloride source, AlCl3-catalyzed regioselective ring-opening of epoxides was merged successfully with the palladium-catalyzed carbonylative cross-coupling of aryl iodides. A variety of the desired 2-chloroethyl benzoates were obtained in moderate to excellent yields with very good substrates compatibility.

A phosphine-free, heterogeneous palladium-catalyzed atom-efficient carbonylative cross-coupling of triorganoindiums with aryl halides leading to unsymmetrical ketones

A phosphine-free heterogeneous palladium-catalyzed carbonylative cross-coupling of triorganoindiums with aryl halides for the synthesis of unsymmetrical ketones has been described.

Palladium-catalyzed intermolecular carbonylative cross-coupling of heteroaryl C(sp2)-H bonds with amines: an efficient strategy for oxidative aminocarbonylation of azoles.

An efficient palladium-catalyzed oxidative aminocarbonylation of azoles has been developed. This system allows for intermolecular carbonylative cross-coupling of aromatic C(sp2)-H bonds with simple amines, which has often been asked for, but has not been realized so far. It provides a straightforward approach to a variety of azol-2-amides.

Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones.

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.

ChemInform Abstract: Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of 1-Halo-1- alkenes with 9-Alkyl-9-BBN Derivatives. A Direct Synthesis of α,. beta.-Unsaturated Ketones.

ChemInform Abstract: Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of 1-Halo-1- alkenes with 9-Alkyl-9-BBN Derivatives. A Direct Synthesis of α,. beta.-Unsaturated Ketones.

ChemInform Abstract: Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Iodoalkanes with 9-Alkyl-9-BBN Derivatives. A Direct and Selective Synthesis of Ketones.

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ChemInform Abstract: Synthesis of Unsymmetrical Biaryl Ketones (IV) via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids (I) with Iodoarenes (II).

ChemInform Abstract: Synthesis of Unsymmetrical Biaryl Ketones (IV) via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids (I) with Iodoarenes (II).

A synthesis of sulfonamide analogs of platensimycin employing a palladium-mediated carbonylation strategy

The monodentate ligand 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane (PA-Ph) is shown to be highly effective in palladium-catalyzed carbonylative cross-coupling. Aryl and vinyl halides were efficiently converted to carboxylic acids, amides and to primary, secondary, and tertiary esters, respectively. Application of the Pd(OAc) 2/PA-Ph (1:1) catalyst system proved critical in the methoxycarbonylation of a functionalized nitroresorcinol halide, allowing convenient access to novel platensimycin sulfonamide analogs.

Applications of Heteroarylboron Compounds to Organic Synthesis

This report deals with our recent results concerning the reaction and synthetic application of boronsubstituted heteroaromatic compounds (1) palladium-catalyzed cross-coupling, carbonylative cross-coupling and tandem cyclization cross-coupling reactions with dialkylpyridylboranes and indolylborates, and their use in the preparation of heterocyclic derivatives and (2) the synthetic application of an intramolecular alkyl migration process in indolylborates for the construction of more elaborate indole derivatives. Keywords: heteroarylboron compound, indole derivatives, tandem cyclizaation

PALLADIUM-CATALYZED ARYLATION AND ARYLOYLATION OF ORGANOSTANNANES WITH TRIARYLBISMUTH(V) DERIVATIVES

The palladium-catalyzed cross-coupling and carbonylative cross-coupling of pentavalent bismuth(V) derivatives with organostannanes have been achieved in CH3CN at room temperature.

Preparation of triarylantimony(V) diacetates and palladium-catalyzed cross-coupling and carbonylative cross-coupling of triarylantimony(V) diacetates and dichlorides with organostannanes

Triarylstibines react with iodobenzene diacetate in dichloromethane to afford triarylantimony(V) diacetates. The cross-coupling and carbonylative cross-coupling of triarylantimony(V) diacetates and dichlorides with organostannanes was accomplished in the presence of PdCl 2 (5 mol%) in CH 3CN at room temperature.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

The carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles (ArI, ArBr, and ArOTf) to yield unsymmetrical biaryl ketones was carried out in anisole at 80 °C in the presence of a palladium catalyst and a base. The reaction selectively proceeded under an atmospheric pressure of carbon monoxide when PdCl2(PPh3)2 (3 mol %)/K2CO3 (3 equiv) were used for aryl iodides and PdCl2(dppf) (3 mol %)/K2CO3 (3 equiv)/KI (3 equiv) for the bromides or the triflates. The carbonylation of arylboronic acids with benzyl halides gave aryl benzyl ketones.

Palladium-Catalyzed Carbonylative Cross-Coupling of Organoboranes with Hypervalent Iodonium Salts: Synthesis of Aromatic Ketones

The cross-coupling reaction of organoboronic acids and carbon monoxide (1 atm) with aryl-, alkenyl-, and alkynyliodonium salts at room temperature afforded unsymmetric aromatic ketones in moderate yields.

Cross-coupling and carbonylative cross-coupling of organofluorosilanes with hypervalent iodonium tetrafluoroborates

The palladium-catalyzed cross-coupling and carbonylative cross-coupling of aryl-, alkenyl-, and alkynylfluorosilanes promoted by fluoride ion with hypervalent aryl-, alkenyliodonium tetrafluoroborates were achieved at room temperature under an atmospheric pressure of carbon monoxide.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction with Triethyl(1-methylindol-2-yl)borate: A Simple Route to 1-Methyl-2-indolyl Ketones

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction with Triethyl(1-methylindol-2-yl)borate: A Simple Route to 1-Methyl-2-indolyl Ketones

New synthetic transformations via organoboron compounds

Abstract

Preparation of 3-acyl-3-cyclobutene-1,2-diones and some related monoacetals

3-(Tri-n-butylstannyl)-3-cyclobutene-1,2-diones and 4-methyl-3-(tri-n-butystannyl)-3-cyclobutene-1,2-dione 2-ethylene acetal participate in palladium/copper-cocatalyzed cross-coupling with acyl halides and in palladium-catalyzed carbonylative cross-coupling with aryl/heteroaryl iodides. The derived 3-acyl-3-cyclobutenediones and cyclobutenedione monoacetals should extend the potential of cyclobutenedione-based synthetic organic methodology

Carbonylative coupling reaction of organofluorosilanes with organic halides promoted by fluoride ion and palldium catalyst

Palladium-catalyzed carbonylative cross coupling reaction of organofluorosilanes with organic halides was achieved in the presence of fluoride ion and an atmospheric pressure of carbon monoxide. Alkenyl- or arylfluorosilanes effectively underwent this reaction with alkenyl or aryl iodides in moderate to good yields. Thus, highly functionalized ketones are readily available without protection of reactive functional group such as aldehyde, ketone, ester, nitrile, and alcohol. For smooth ketone formation, use of organofluorosilanes is essential; tetraorganosilanes like aryl(trimethyl)silanes, upon reaction with aryl iodides, gave aroyl fluorides instead.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of 1-Halo-1-alkenes with 9-Alkyl-9-BBN Derivatives. A Direct Synthesis of α,β-Unsaturated Ketones

Abstract The synthesis of α,β-unsaturated ketones by means of the palladium-catalyzed cross-coupling reaction between 9-alkyl-9-borabicyclo[3.3.1]nonanes (9-R-9-BBN) and 1-halo-1-alkenes under carbon monoxide atmosphere is described.