Palladacycle-Catalyzed Deacetonative Sonogashira Coupling of Aryl Propargyl Alcohols with Aryl Chlorides

An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides is described. The reaction proceeded smoothly with the catalyst system of palladacycle/Xphos. This result represents the first successful deacetonative Sonogashira version for electron-poor, electron-neutral, and even inactive sterically hindered electron-rich aryl chlorides

Palladacycle-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Chlorides under Air

A highly efficient and practical protocol for palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides was developed. The reaction could proceed smoothly in air within 3 h under optimized reaction conditions (1 mol % of palladacycle, 4 mol % of Xphos, 2.0 equiv of K₂CO₃ in xylene/H₂O), affording the corresponding internal alkynes in mostly good to excellent yields. Remarkably, this result represents the first successful examples of this type of decarboxylative cross-coupling using electron-poor, electron-neutral and even inactive sterically hindered electron-rich aryl chlorides as the starting materials

“One-Pot” Approach to 8‑Acylated 2‑Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline <i>N</i>‑Oxides

A “one-pot” facile and efficient protocol for 8-acylated 2-quinolinones has been developed through palladium-catalyzed acylation of quinoline <i>N</i>-oxides, which proceeds with high selectivity at the C8-position. The desired products were isolated in up to 95% yield and good functional group tolerance. A palladacycle was isolated from the catalytic process and proposed as a key intermediate

Iridium-Catalyzed Direct C–H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature

Ir­(III)-catalyzed direct C–H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product

“One-Pot” Approach to 8‑Acylated 2‑Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline <i>N</i>‑Oxides

A “one-pot” facile and efficient protocol for 8-acylated 2-quinolinones has been developed through palladium-catalyzed acylation of quinoline <i>N</i>-oxides, which proceeds with high selectivity at the C8-position. The desired products were isolated in up to 95% yield and good functional group tolerance. A palladacycle was isolated from the catalytic process and proposed as a key intermediate

“One-Pot” Approach to 8‑Acylated 2‑Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline <i>N</i>‑Oxides

A “one-pot” facile and efficient protocol for 8-acylated 2-quinolinones has been developed through palladium-catalyzed acylation of quinoline <i>N</i>-oxides, which proceeds with high selectivity at the C8-position. The desired products were isolated in up to 95% yield and good functional group tolerance. A palladacycle was isolated from the catalytic process and proposed as a key intermediate

Iridium-Catalyzed Direct C–H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature

Ir­(III)-catalyzed direct C–H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product

C8-Selective Acylation of Quinoline <i>N</i>‑Oxides with α‑Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C–H Bond Activation

A facile and efficient protocol for palladium-catalyzed C8-selective acylation of quinoline <i>N</i>-oxides with α-oxocarboxylic acids has been developed. In this approach, <i>N</i>-oxide was utilized as a stepping stone for the remote C–H functionalization. The reactions proceeded efficiently under mild reaction conditions with excellent regioselectivity and broad functional group tolerance

“One-Pot” Approach to 8‑Acylated 2‑Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline <i>N</i>‑Oxides

A “one-pot” facile and efficient protocol for 8-acylated 2-quinolinones has been developed through palladium-catalyzed acylation of quinoline <i>N</i>-oxides, which proceeds with high selectivity at the C8-position. The desired products were isolated in up to 95% yield and good functional group tolerance. A palladacycle was isolated from the catalytic process and proposed as a key intermediate

Copper-Mediated Oxidative Decarboxylative Coupling of Arylpropiolic Acids with Dialkyl H‑Phosphonates in Water

An efficient, mild, and generally applicable protocol for copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water has been developed. Note that the reaction could proceed smoothly under air at relatively low temperature (60 °C), and the addition of isopropanol could successfully suppress the decomposition of dialkyl H-phosphonates in water