Activation of Primary Amines by Copper(I)-Based Lewis Acid Promoters in the Solventless Synthesis of Secondary Propargylamines

Abstract

Primary amines are activated by copper(I)-based Lewis acid promoters in an A³-coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO₄/NaI system, a practical precursor of the in situ generated effective CuI/I₂ system, that worked well, but only in a restricted number of examples. Substitution of I₂ with CeCl₃·7H₂O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

Key words

propargylamines - A³ coupling - primary amines - copper - cerium trichloride - Lewis acids

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