Take two: α‐Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium‐catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different CC bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O‐substituted quaternary carbon center.
ortho-Aminated vinylarene derivatives were obtained via a reaction of aryl iodides, N-benzoyloxyamines, and N-tosylhydrazones. This approach involves a palladium-catalyzed, norbornene-mediated ortho-amination/N-tosylhydrazone insertion reaction. In this transformation, one C-N bond and one C-C bond are formed and an amine group is introduced at the ortho position successfully.
A new palladium-catalyzed three-component coupling involved acylation/alkenylation of aryl iodide is reported. The reaction was carried out with readily available starting materials and gave the ortho-acylated styrene in moderate to good yields. Compared to previous Catellani-Lautens reaction, this reaction is the first example of introducing an acyl group at the ortho-position of aryl iodides. The proposed Pd IV complex, generated via oxidative addition of the carboxylic anhydrides, is a key intermediate for this transformation.
An iodine-promoted one-pot radical cyclization reaction of 1,6-enynes with sulfonyl hydrazides to provide five-membered and hexatomic ring sulfonylated products under the same conditions is established. This reaction proceeded smoothly in water and gave the corresponding products by using I2/TBHP instead of expensive and toxic catalysts with C-S and C-I bond formed in one step. This method also allowed easy access to significant functional sulfones for potential applications in medicinal and organic chemistry.
Two different cyclic amino esters are synthesized by palladium-catalyzed cross-coupling reaction of diazoesters with N-substituted-2-iodoanilines. Aryldiazoacetates lead to cyclic α-amino esters with an α-quaternary carbon centre in the presence of CO. Additionally, arylvinyldiazoacetates afford cyclic α,β-unsaturated γ-amino esters.
A novel method of a palladium-catalyzed/norbornene-mediated intramolecular C-H activation/N-tosylhydrazones insertion reaction is developed. In this process, various bicyclic or tricyclic substituted vinylarenes are obtained with high efficiency under mild conditions.
Coupling shakes this couple: Dynamics and the IR absorption spectrum of the protonated water dimer are reported by full‐dimensional quantum simulation. Strong couplings between the IR‐active proton‐transfer motion and low‐frequency, large‐amplitude torsional modes are clearly identified, and their role in the cluster dynamics is explained. These couplings are responsible for the characteristic doublet at about 1000 cm−1.
Palladium-catalyzed carbene migratory insertion-cyclization reactions were reported, delivering dihydronaphthalene and indene derivatives in moderate to good yields. A three-component cross-coupling was also developed. The reactions are easy to handle, under mild conditions and various functional groups are tolerated.
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