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Synthesis of Oxygenated Heterocyclic Compounds via Gold-Catalyzed Functionalization of π-Systems

Part of the Topics in Heterocyclic Chemistry book series (TOPICS,volume 46)

Abstract

During the last decade, there has been an impressive amount of new reactions catalyzed by gold (I or III) complexes, many of which lead to oxygen heterocycles in novel, practical, and efficient ways. In this chapter we have selected the most representative examples of the use of gold catalysis for the synthesis of oxygenated heterocycles, with an organization based on the type of reaction. Each section pretends to give an overview of the potential of each particular strategy and its usefulness to prepare synthetically relevant oxygenated rings. Heterocyclic systems that contain other heteroatoms in addition to oxygen have been essentially excluded, as well as those examples in which the oxygen atoms merely acts as a connecting element between two reactive functional groups.

Keywords

  • Cyclization
  • Cycloaddition
  • Gold catalysis
  • Heterocycles
  • Organometallic catalysis
  • Oxacycles

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Notes

  1. 1.

    In Sect. 2.4 a series of tandem processes, where this vinyl gold species are used as key intermediates, are discussed.

  2. 2.

    For related gold(I)-catalyzed tandem cyclization reactions of alkynylindoles with pendant hydroxyl groups, see [99101].

  3. 3.

    For related cyclizations, see also [46, 109114].

  4. 4.

    For a related example, see [131].

  5. 5.

    For a related example, see [142].

  6. 6.

    For a review summarizing these and other Au(I)/Au(III) oxidative couplings, see [139].

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Mascareñas, J.L., López, F. (2016). Synthesis of Oxygenated Heterocyclic Compounds via Gold-Catalyzed Functionalization of π-Systems. In: Bandini, M. (eds) Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 46. Springer, Cham. https://doi.org/10.1007/7081_2015_5006

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