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Synthesis of Heterocycles via Metal-Catalyzed Domino/One-Pot Reactions That Generate a C—N or C—O Bond

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Book cover Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 32))

Abstract

This chapter focuses on transition metal-catalyzed domino (cascade) or one-pot syntheses of heterocycles via the formation of a carbon–nitrogen, –oxygen, or –sulfur bond. A precise classification of domino, one-pot, and tandem reactions is given. However, despite that rather strict definition, the chapter includes a variety of processes that are important from a mechanistic and synthetic point of view. These are methods which showcase both ingenious and efficient reaction design while simultaneously aiming to minimize deleterious byproduct formation as well as uneconomical workup and purification steps. While there are several types of protocols highlighted within this section, there is a larger emphasis on transition metal-catalyzed cycloisomerization methods, the utility of gem-dihaloolefins, and C—H functionalization protocols within the framework of domino catalysis.

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Notes

  1. 1.

    There have been recorded instances in literature by Bolm, Buchwald, and others where it has been determined that trace metal impurities are the catalytically active species in transition metal-catalyzed reactions. This is especially relevant in many iron-catalyzed methods.

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Acknowledgments

The authors would like to thank the Natural Sciences and Engineering Council of Canada (NSERC) and the University of Toronto for financial support. NSERC/Merck-Frosst Canada is thanked for an Industrial Research Chair. JK thanks the Deutsche Forschungsgemeinschaft for a postdoctoral fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Davenport Research Laboratories, University of Toronto, 80 St. George Street, Toronto, ON, Canada, M5S 3H6

    Juliane Keilitz & Mark Lautens

  2. Novartis Institutes for Biomedical Research, 250 Massachusetts Avenue, Cambridge, MA, 02142, USA

    Hasnain A. Malik

Authors
  1. Juliane Keilitz
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  2. Hasnain A. Malik
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  3. Mark Lautens
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Corresponding author

Correspondence to Mark Lautens .

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Editors and Affiliations

  1. Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA

    John P. Wolfe

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Keilitz, J., Malik, H.A., Lautens, M. (2013). Synthesis of Heterocycles via Metal-Catalyzed Domino/One-Pot Reactions That Generate a C—N or C—O Bond. In: Wolfe, J. (eds) Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds. Topics in Heterocyclic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2013_106

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