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.
Highlights
Propargylamines are useful synthetic scaffolds broadly exploited as precursors of heterocyclic compounds, such as quinolones [1a], phenanthrolines [1b], pyrroles [1c], pyrrolidines [1d], indolizines [1e] or oxazolidinones [1f], among others [2]
We present a comprehensive review on the synthesis of propargylamines by the catalytic coupling of Csp3-H bonds adjacent to nitrogen with Csp-H bonds of terminal alkynes [Scheme 1, eq (5)]
Concluding this review, we can say that the crossdehydrogenative coupling (CDC) of amines and terminal alkynes is a convenient and green approach to the synthesis of propargylamines
Summary
Propargylamines are useful synthetic scaffolds broadly exploited as precursors of heterocyclic compounds, such as quinolones [1a], phenanthrolines [1b], pyrroles [1c], pyrrolidines [1d], indolizines [1e] or oxazolidinones [1f], among others [2] They have been utilized as starting materials for transition-metal catalyzed Csp3-H and Csp3Csp activation [3], and as intermediates in the total synthesis of some natural and pharmaceutical products [4]. The propargylamine unit can be found in diverse bioactive compounds [5], some of which have been proven to be potent anti-apoptotic agents that protect neurons against cell death in cellular and animal models of neurodegenerative disorders They have been shown to delay the necessity for symptomatic therapy in untreated Parkinson’s disease patients, results that are consistent with the neuroprotection role of this type of compounds [6]. We present a comprehensive review on the synthesis of propargylamines by the catalytic coupling of Csp3-H bonds adjacent to nitrogen with Csp-H bonds of terminal alkynes [Scheme 1, eq (5)]
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