N -Heterocyclic carbene–carbodiimide (NHC–CDI) betaine adducts: synthesis, characterization, properties, and applications
Name
d0sc06465c.pdf
Description
Published version
Size
1.83 MB
Format
Adobe PDF
Checksum (MD5)
68a07f51a10228840ab5f0d829cbb084
Author(s)
Lamb, Jessica R
Brown, Christopher M
Johnson, Jeremiah A
Date Issued
2021
Journal
Chemical Science
Publisher
Royal Society of Chemistry (RSC)
Citation
Lamb, Jessica R, Brown, Christopher M and Johnson, Jeremiah A. 2021. "N -Heterocyclic carbene–carbodiimide (NHC–CDI) betaine adducts: synthesis, characterization, properties, and applications." Chemical Science, 12 (8).
Version
Final published version
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution 3.0 unported license
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DOI of Published Version
https://doi.org/10.1039/D0SC06465C
