Synthesis Of Alkyl Aryl Ketones Research Articles

Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

AbstractAlkyl aryl ketones are important structures with applications in many areas of chemistry. Hence, efficient procedures for their production are particularly attractive. In this communication, a general and efficient carbonylative cross‐coupling of aryl iodides and unactivated alkyl bromides is presented. By using a simple palladium catalyst, a series of alkyl aryl ketones were synthesized in moderate to excellent yields from readily available alkyl and aryl halides in an In‐Ex tube with formic acid as the CO source. In this study both primary and secondary alkyl bromides/iodides were suitable coupling partners. Additionally, this method can also be employed for the late‐stage functionalization of complex natural products and polyfunctionalized molecules.magnified image

ChemInform Abstract: Palladium Catalyzed Decarboxylative Acylation of Arylboronic Acid with Ethyl Cyanoacetate as a New Acylating Agent: Synthesis of Alkyl Aryl Ketones.

Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.

Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: synthesis of alkyl aryl ketones

The versatile, one-pot synthesis of a series of alkyl aryl ketones is described using ethyl cyanoacetate as a new acylating agent.

ChemInform Abstract: Synthesis of Alkyl Aryl Ketones by Pd/Light Induced Carbonylative Cross‐Coupling of Alkyl Iodides and Arylboronic Acids.

Alkyl aryl ketones were synthesized by the carbonylative cross-coupling reaction of alkyl iodides and arylboronic acids under combined Pd/light conditions. In this reaction, it is likely that an acylpalladium species would be formed via carbonylation of the alkyl radical, which would then undergo transmetalation of an arylboronic acid to give the corresponding acyl(aryl)palladium species, ready to undergo reductive elimination to yield the alkyl aryl ketone.

ChemInform Abstract: Palladium‐Catalyzed Addition of Potassium Aryltrifluoroborates to Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones, Diketone Compounds, and 2‐Arylbenzo[b]furans.

A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential addition and intramolecular annulation reactions. The methodology accepted a wide range of substrates and is applicable to library synthesis.

Palladium-Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2-Arylbenzofurans

An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions.

Synthesis of Alkyl Aryl Ketones by Pd/Light Induced Carbonylative Cross-Coupling of Alkyl Iodides and Arylboronic Acids

Alkyl aryl ketones were synthesized by the carbonylative cross-coupling reaction of alkyl iodides and arylboronic acids under combined Pd/light conditions. In this reaction, it is likely that an acylpalladium species would be formed via carbonylation of the alkyl radical, which would then undergo transmetalation of an arylboronic acid to give the corresponding acyl(aryl)palladium species, ready to undergo reductive elimination to yield the alkyl aryl ketone.

Palladium-Catalyzed Addition of Potassium Aryltrifluoroborates to Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones, Diketone Compounds, and 2-Arylbenzo[b]furans

A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential addition and intramolecular annulation reactions. The methodology accepted a wide range of substrates and is applicable to library synthesis.

Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids

The synthesis of alkyl aryl ketones using a mandelic acid dioxolanone as a synthetic equivalent (Umpolung) of the benzoyl carbanion is reported. The methodology involves alkylation of the mandelic acid dioxolanone, hydrolysis of the dioxolanone moiety in the alkylated products and oxidative decarboxylation of the resulting alpha-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co (III) complex in the presence of pivalaldehyde under very mild conditions.

Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids

The synthesis of alkyl aryl ketones using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion is reported (Umpolung). The methodology involves alkylation of methyl mandelate, hydrolysis of the ester group and oxidative decarboxylation of the resulting α-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co(III) complex in the presence of pivalaldehyde under very mild and advantageous conditions. The procedure is also applied to methyl mandelates substituted on the aromatic ring.

Palladium-catalyzed iminocarbonylative cross-coupling reaction between haloarenes, t-BuNC, and 9-alkyl-9-BBN derivatives. Synthesis of alkyl aryl ketones

The cross-coupling reaction between 9-alkyl-9-BBN derivatives, t-butylisocyanide, and haloarenes was carried out in dioxane at 50°C in the presence of K 3PO 4 and a catalytic amount of Pd(PPh 3) 4. The reaction provides alkyl aryl ketones in high yields after hydrolysis of the ketimine intermediates.

The coupling reaction of copper(I) methyltrialkylborates with aroyl chlorides. A convenient synthesis of alkyl aryl ketones from organoboranes

The coupling reaction of copper(I) methyltrialkylborates with aroyl chlorides. A convenient synthesis of alkyl aryl ketones from organoboranes

A facile reaction of trialkylboranes with α-azidostyrene. A convenient and general synthesis of alkyl aryl ketones via hydroboration

A facile reaction of trialkylboranes with α-azidostyrene. A convenient and general synthesis of alkyl aryl ketones via hydroboration

Condensation of 2-Aryl-1,3-dioxolanes with Alkyllithium Reagents. A New Synthesis of Alkyl Aryl Ketones from Aromatic Aldehydes1

Condensation of 2-Aryl-1,3-dioxolanes with Alkyllithium Reagents. A New Synthesis of Alkyl Aryl Ketones from Aromatic Aldehydes¹