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

C. Cimarelli,Federica Navazio,Federico Rossi,Fabio Del Bello,E. Marcantoni

Published 2019 in Synthesis

ABSTRACT

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.

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