Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes

David Nelson, Jeremy Praetorius, Cathleen Crudden

Research output: Chapter in Book/Report/Conference proceedingChapter

2 Citations (Scopus)

Abstract

NHC–transition metal complexes are described in terms of their synthesis, stability and utility as catalytic precursors. After a review of the more common methods of synthesis, the known decomposition reactions are described. These include displacement of the NHC from the metal coordination sphere, reductive elimination of the NHC and adjacent ligands, and C–H/C–C or C–N activation of the NHC ligand, in addition to other pathways such as migratory insertion reactions. With these decomposition routes in mind, the approaches required to prepare NHC–metal complexes that are resistant to degradation are depicted. Finally, useful methods for generating active catalysts from NHC–metal complexes are described, including, in some cases, results gleaned during studies of decomposition pathways. Taken together, these sections will provide the reader with a detailed knowledge of the expected stability of typical NHC complexes, in addition to methods of generating active catalysts from them.
Original languageEnglish
Title of host publicationN-Heterocyclic Carbenes
Subtitle of host publicationFrom Laboratory Curiosities to Efficient Synthetic Tools
EditorsSilvia Diez Gonzalez
PublisherRoyal Society of Chemistry
Pages46-98
Number of pages53
Edition2
DOIs
Publication statusPublished - 8 Nov 2016

Publication series

NameCatalysis Series
PublisherRoyal Society of Chemistry

Fingerprint

Chemical activation
Decomposition
Ligands
Catalysts
Coordination Complexes
Metals
Degradation
carbene

Keywords

  • synthesis
  • activation
  • decomposition
  • N-heterocyclic carbene complexes
  • metal complexes
  • catalytic precursors
  • ligands
  • migratory insertion reactions

Cite this

Nelson, D., Praetorius, J., & Crudden, C. (2016). Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes. In S. Diez Gonzalez (Ed.), N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools (2 ed., pp. 46-98). (Catalysis Series). Royal Society of Chemistry. https://doi.org/10.1039/9781782626817-00046
Nelson, David ; Praetorius, Jeremy ; Crudden, Cathleen. / Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes. N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools. editor / Silvia Diez Gonzalez. 2. ed. Royal Society of Chemistry, 2016. pp. 46-98 (Catalysis Series).
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Nelson, D, Praetorius, J & Crudden, C 2016, Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes. in S Diez Gonzalez (ed.), N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools. 2 edn, Catalysis Series, Royal Society of Chemistry, pp. 46-98. https://doi.org/10.1039/9781782626817-00046

Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes. / Nelson, David; Praetorius, Jeremy; Crudden, Cathleen.

N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools. ed. / Silvia Diez Gonzalez. 2. ed. Royal Society of Chemistry, 2016. p. 46-98 (Catalysis Series).

Research output: Chapter in Book/Report/Conference proceedingChapter

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N2 - NHC–transition metal complexes are described in terms of their synthesis, stability and utility as catalytic precursors. After a review of the more common methods of synthesis, the known decomposition reactions are described. These include displacement of the NHC from the metal coordination sphere, reductive elimination of the NHC and adjacent ligands, and C–H/C–C or C–N activation of the NHC ligand, in addition to other pathways such as migratory insertion reactions. With these decomposition routes in mind, the approaches required to prepare NHC–metal complexes that are resistant to degradation are depicted. Finally, useful methods for generating active catalysts from NHC–metal complexes are described, including, in some cases, results gleaned during studies of decomposition pathways. Taken together, these sections will provide the reader with a detailed knowledge of the expected stability of typical NHC complexes, in addition to methods of generating active catalysts from them.

AB - NHC–transition metal complexes are described in terms of their synthesis, stability and utility as catalytic precursors. After a review of the more common methods of synthesis, the known decomposition reactions are described. These include displacement of the NHC from the metal coordination sphere, reductive elimination of the NHC and adjacent ligands, and C–H/C–C or C–N activation of the NHC ligand, in addition to other pathways such as migratory insertion reactions. With these decomposition routes in mind, the approaches required to prepare NHC–metal complexes that are resistant to degradation are depicted. Finally, useful methods for generating active catalysts from NHC–metal complexes are described, including, in some cases, results gleaned during studies of decomposition pathways. Taken together, these sections will provide the reader with a detailed knowledge of the expected stability of typical NHC complexes, in addition to methods of generating active catalysts from them.

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Nelson D, Praetorius J, Crudden C. Synthesis, activation, and decomposition of N-heterocyclic carbene-containing complexes. In Diez Gonzalez S, editor, N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools. 2 ed. Royal Society of Chemistry. 2016. p. 46-98. (Catalysis Series). https://doi.org/10.1039/9781782626817-00046