Title:Synthesis of Propargylamines by Cross-Dehydrogenative Coupling
Volume: 6
Issue: 2
Author(s): Francisco Alonso*, Irene Bosque, Rafael Chinchilla, José Carlos Gonzalez-Gomez and David Guijarro
Affiliation:
- Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante,Spain
Keywords:
Asymmetric synthesis, cross-dehydrogenative coupling, green chemistry, homogeneous catalysis, heterogeneous
catalysis, photoredox catalysis, propargylamines, tetrahydroisoquinolines.
Abstract: Propargylamines are versatile compounds for heterocyclic synthesis, some of which are
current drugs prescribed to treat patients with Parkinson’s disease. There are different methods to synthesize
propargylamines, however, modern chemistry has moved progressively to rely on new strategies
that meet the principles of Green Chemistry. In this context, propargylamines are readily accessible
by the cross-dehydrogenative coupling (CDC) of two C-H bonds (i.e., NCsp3-H and Csp-H
bonds); surely, CDC can be considered the most atom-economic and efficient manner to form C-C
bonds. The aim of this review is to provide a comprehensive survey on the synthesis of propargylamines
by the CDC of amines and terminal alkynes from three fronts: (a) transition-metal homogeneous
catalysis, (b) transition-metal heterogeneous catalysis and (c) photoredox catalysis. A section dealing
with the asymmetric synthesis of chiral propargylamines is also included. Special attention is also
devoted to the proposed reaction mechanisms.