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In the presence of catalytic [Ru( p-cym)I2]2 and the base guanidine carbonate, benzoic acids react with internal alkynes to give the corresponding 2-vinylbenzoic acids. This alkyne hydroarylation is generally applicable to diversely substituted electron-rich and electron-poor benzoic and acrylic acids. Aryl(alkyl)acetylenes react regioselectively with formation of the alkyl-branched hydroarylation products, and propargylic alcohols are converted into γ-alkylidene-δ-lactones. The hydroarylation can also be conducted decarboxylatively with a different choice of catalyst and reaction conditions. This reaction variant, which does not proceed via intermediate formation of 2-vinylbenzoic acids, opens up a regioselective, waste-minimized synthetic entry to vinylarenes. [ABSTRACT FROM AUTHOR]

A pH-controlled monophasic/biphasic switchable system has been developed as a green and novel strategy for homogeneous catalyst recycling, which has been successfully applied to the Cu-NHC-catalyzed carboxylation of organoboronic esters and benzoxazole with carbon dioxide. Additionally, the present strategy could also be extended to the Ag-NHC-catalyzed carboxylation of terminal alkyne. The tertiary amine-functionalized catalysts could be used for at least four times with a slight loss of activity. [ABSTRACT FROM AUTHOR]

N-Heterocyclic carbene Cu and Ag complexes are shown to catalyze the carboxylation of organoboric esters, benzoxazole, and terminal alkynes. [ABSTRACT FROM AUTHOR]

A graphical abstract of the article "Regioselective C-H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups" is presented.