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A copper-catalyzed aminobenzannulation of (o-alkynyl)arylketones with amines has been developed. This method features the use of a cheap copper catalyst, the facile annulation involving various amines, and the good functional group tolerance.

The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl)benzaldimines to give the corresponding isoquinolinium intermediates.

The convenient, efficient protocol for the phosphorylation of the title compounds furnishes 2-diarylphosphoryl-substituted products under mild conditions.

Both 3-aryl and 3-alkyl substituted isocoumarins are synthesized by a Rh(III)-catalyzed C—H activation/annulation reaction of electron-rich germinal-substituted vinyl acetates and arylcarboxylic acids.

Natural Science Foundation of China [21072161, 21302157]; National Basic Research Program of China (973 Program) [2012CB821600]; Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT); Fundamental Research Funds for the Central Universities