Dehydrogenative cross-coupling reaction of primary anilines, secondary anilines, carboxamides, and sulfonamides with 1,3-diarylpropenes to form a series of allylic amines promoted by DDQ have been realized. Both monoallylation and diallylation products can be selectively synthesized when primary anilines are used as the starting materials. The method may provide a wide scope of allylamines in scientific research including biologically active compound library construction.
An efficient oxidative cross-coupling reaction between 1,3-diarylpropenes and indoles in the presence of palladium chloride was achieved with 2,3-dichloro-5,6-dicyanoquinone (DDQ) as oxidant. The reaction afforded 1,3-diphenylallylindoles in moderate to high yields under mild conditions, thus providing a novel methodology to synthesize the respective products.
A general and transition-metal-free method for the construction of the carbazol-4-amine motif via a vinylogous Michael addition/cyclization/isomerization/elimination reaction of 3-nitroindoles with alkylidene malononitriles has been developed. This novel methodology allows the facile synthesis of a series of di- and trisubstituted carbazol-4-amine derivatives in moderate to good yields. A gram-scale experiment was successfully performed, highlighting the practicability of this method. Moreover, this strategy is also applicable to 3-nitrobenzothiophene, affording the corresponding dibenzo[ b, d]thiophen-1-amine derivatives in moderate yields.
A method for the synthesis of (Z)-vinyl chalcogenides by the coupling of vinyl bromides with thiols or diphenyl diselenide using copper(I) salts as catalysts in ionic liquids based on amino acids is reported. The desired vinyl chalcogenides were obtained in good to excellent yields with retention of stereochemistry. The ionic liquids play multiple roles in the reaction: they act as solvent, base, and excellent promoter for the copper-catalyzed coupling reactions.
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