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Issue 8, 2021
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N-Heterocyclic carbene–carbodiimide (NHC–CDI) betaine adducts: synthesis, characterization, properties, and applications

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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. This Perspective is 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.

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

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Article information


Submitted
24 Nov 2020
Accepted
18 Jan 2021
First published
19 Jan 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 2699-2715
Article type
Perspective

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

J. R. Lamb, C. M. Brown and J. A. Johnson, Chem. Sci., 2021, 12, 2699
DOI: 10.1039/D0SC06465C

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