Palladium-Catalyzed Regioselective Carbonylation of C–H Bonds of <i>N</i>‑Alkyl Anilines for Synthesis of Isatoic Anhydrides

A Pd-catalyzed regioselective C–H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions

Palladium-Catalyzed Regioselective Carbonylation of C–H Bonds of <i>N</i>‑Alkyl Anilines for Synthesis of Isatoic Anhydrides

A Pd-catalyzed regioselective C–H bond carbonylation of <i>N</i>-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available <i>N</i>-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions

Highly Regioselective Synthesis of Benz[<i>a</i>]anthracene Derivatives via a Pd-Catalyzed Tandem C−H Activation/Biscyclization Reaction

A palladium-catalyzed tandem C−H activation/biscyclization reaction of propargylic carbonates with terminal alkynes was determined, which allowed the tetracyclic benz[a]anthracene framework to be constructed with high regioselectivity. A possible mechanism for this tandem C−H activation/biscyclization process was discussed

Palladium-Catalyzed Regioselective Carbonylation of C–H Bonds of <i>N</i>‑Alkyl Anilines for Synthesis of Isatoic Anhydrides

A Pd-catalyzed regioselective C–H bond carbonylation of <i>N</i>-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available <i>N</i>-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions

Palladium-Catalyzed Hydroalkoxycarbonylation and Hydroxycarbonylation of Cyclopent-3-en-1-ols: Divergent Synthesis of Bridged Cyclic Lactones and β,γ-Unsaturated Carboxylic Acids

Herein, we report a palladium-catalyzed hydroalkoxycarbonylation and hydroxycarbonylation of cyclopent-3-en-1-ols to form bridged bicyclic lactones and β,γ-unsaturated carboxylic acid. The divergent reactivity of cyclopent-3-en-1-ols is mainly tuned by the palladium catalyst and ligands. The reaction occurs additive-free and has a broad substrate scope. Several valuable synthetic and medical intermediates are accessible through this protocol

Palladium-Catalyzed Regioselective Carbonylation of C–H Bonds of <i>N</i>‑Alkyl Anilines for Synthesis of Isatoic Anhydrides

A Pd-catalyzed regioselective C–H bond carbonylation of <i>N</i>-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available <i>N</i>-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions

Highly Regioselective Synthesis of Benz[<i>a</i>]anthracene Derivatives via a Pd-Catalyzed Tandem C−H Activation/Biscyclization Reaction

A palladium-catalyzed tandem C−H activation/biscyclization reaction of propargylic carbonates with terminal alkynes was determined, which allowed the tetracyclic benz[a]anthracene framework to be constructed with high regioselectivity. A possible mechanism for this tandem C−H activation/biscyclization process was discussed

Copper-Promoted 6-<i>endo-trig</i> Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines

A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH

Palladium-Catalyzed Oxidative Carbonylation of Aromatic C–H Bonds of <i>N</i>‑Alkylanilines with CO and Alcohols for the Synthesis of <i>o</i>‑Aminobenzoates

A Pd­(II)-catalyzed C–H monocarbonylation of <i>N</i>-alkylanilines for the synthesis of <i>o</i>-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding <i>o</i>-aminobenzoates in good yields under mild balloon pressure of CO

Synthesis of Enamides via Rh/C-Catalyzed Direct Hydroacylation of Ketoximes

Enamides were efficiently prepared via a novel Rh/C-catalyzed direct hydroacylation of ketoximes. Up to 88% isolated yield of enamides were obtained with this method. Subsequent asymmetric hydrogenation of the enamides with Rh/DuanPhos complex gave the corresponding chiral amine in excellent enantioselectivities (up to 99.7% ee)