Dipropargyl amines are synthesized by a double direct alkynylation of primary followed by secondary imines formed in situ during an efficient, five-component, one-pot coupling reaction cocatalyzed by ruthenium and copper in water.

Abstract:The preparation of tetrasubstituted isoindolines from three alkyne units, two aldehyde units and a primary amine via three consecutive reactions, two aldehyde-amine-alkyne couplings (A 3 -couplings) and a final [2 + 2 + 2] cycloaddition, in a single synthetic operation, is described. The A 3 -couplings are catalyzed by copper bromide and the cycloaddition is catalyzed by Wilkinsons catalyst. It was found that many catalysts known to be efficient at the cycloaddition step were not suitable when this step was part of the tandem reaction sequence. Wilkinsons catalyst was found to be unique in its suitability for the overall domino reaction sequence.

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Tetrasubstituted isoindoles are prepared in a single synthetic operation from a primary aniline, three phenylacetylene units, and two formaldehyde units via three consecutive reactions, two aldehyde-amine-alkyne couplings catalyzed by CuBr, and a final [2 + 2 + 2] cycloaddition catalyzed by the Wilkinson's catalyst. -(BONFIELD, E. R.; LI*, C.-J.; Adv.

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