Intramolecular C(sp3)–H Bond Amination Strategies for the Synthesis of Saturated N-containing Heterocycles

Authors

  • Jiayu Zhang Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avinguda Països Catalans 16, Tarragona 43007, Spain
  • Mónica H. Pérez-Temprano Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avinguda Països Catalans 16, Tarragona 43007, Spain;, Email: mperez@iciq.es

DOI:

https://doi.org/10.2533/chimia.2020.895

Keywords:

Amination, C–h functionalization, Catalysis, Cyclization, Heterocycle

Abstract

The selective functionalization of C(sp3)–H bonds via intramolecular amination reactions represents a very attractive strategy for the construction of saturated N-containing heterocycles (SNHets). Over the past de- cades, the chemical community has devoted its efforts towards expanding the synthetic toolbox with the aim of facilitating access to these key fragments in a controllable, reproducible and efficient manner. This review covers selected examples of the most recent advances in intramolecular C(sp3)–N bond-forming reactions by three main approaches: (1) the Hofmann-Löffler-Freytag (HLF) reaction; (2) transition-metal-catalyzed nitrene C(sp3)–H inser- tion; and (3) transition-metal-catalyzed ligand-assisted C(sp3)–N bond-forming reactions via a reductive elimination step. We will discuss reactivity, selectivity and the major mechanistic insights into these transformations.

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Published

2020-11-25

How to Cite

[1]
J. Zhang, M. H. Pérez-Temprano, Chimia 2020, 74, 895, DOI: 10.2533/chimia.2020.895.