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Synthesis of Propargylamines by Cross-Dehydrogenative Coupling

[ Vol. 6 , Issue. 2 ]

Author(s):

Francisco Alonso*, Irene Bosque, Rafael Chinchilla, José Carlos Gonzalez-Gomez and David Guijarro   Pages 105 - 126 ( 22 )

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.

Keywords:

Asymmetric synthesis, cross-dehydrogenative coupling, green chemistry, homogeneous catalysis, heterogeneous catalysis, photoredox catalysis, propargylamines, tetrahydroisoquinolines.

Affiliation:

Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Instituto de Síntesis Organica and Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante

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