Synthesis 2019; 51(11): 2387-2396
DOI: 10.1055/s-0037-1612253
paper
© Georg Thieme Verlag Stuttgart · New York

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

a  School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy   Email: cristina.cimarelli@unicam.it
,
Federica Navazio
a  School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy   Email: cristina.cimarelli@unicam.it
,
Federico V. Rossi
a  School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy   Email: cristina.cimarelli@unicam.it
,
Fabio Del Bello
b  School of Pharmacy, Medicinal Chemistry Unit, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy
,
Enrico Marcantoni
a  School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy   Email: cristina.cimarelli@unicam.it
› Author Affiliations
This work was carried out under the framework of the University Research Project ‘Chemical Swiss tools to treat tumors, metastases and infections’ supported by the University of Camerino (FAR 2014-2015).
Further Information

Publication History

Received: 12 November 2018

Accepted after revision: 24 January 2019

Publication Date:
11 March 2019 (eFirst)

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.

Supporting Information

 
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