N-Heterocyclic carbene-carbodiimide (NHC-CDI) betaine adducts: synthesis, characterization, properties, and applications

Jessica R. Lamb, Christopher M. Brown, Jeremiah A. Johnson

Research output: Contribution to journalArticlepeer-review

Abstract

N-Heterocyclic carbenes (NHCs) are an important class of reactive organic molecules used as ligands, organocatalysts, and σ-donors in a variety of electroneutral ylide or betaine adducts with main-group compounds. An emerging class of betaine adducts made from the reaction of NHCs with carbodiimides (CDIs) form zwitterionic amidinate-like structures with tunable properties based on the highly modular NHC and CDI scaffolds. The adduct stability is controlled by the substituents on the CDI nitrogens, while the NHC substituents greatly affect the configuration of the adduct in the solid state. ThisPerspectiveis intended as a primer to these adducts, touching on their history, synthesis, characterization, and general properties. Despite the infancy of the field, NHC-CDI adducts have been applied as amidinate-type ligands for transition metals and nanoparticles, as junctions in zwitterionic polymers, and to stabilize distonic radical cations. These applications and potential future directions are discussed.

Original languageEnglish (US)
Pages (from-to)2699-2715
Number of pages17
JournalChemical Science
Volume12
Issue number8
DOIs
StatePublished - Jan 19 2021
Externally publishedYes

Bibliographical note

Funding Information:
We acknowledge the National Science Foundation (NSF CHE-1904867) for support of this work. J. R. L. gratefully acknowledges the National Institutes of Health for a postdoctoral fellowship (1F32GM126913-01A1).

Publisher Copyright:
© The Royal Society of Chemistry 2021.

PubMed: MeSH publication types

  • Journal Article
  • Review

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