Issue 8, 2021

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

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

Article information

Article type
Perspective
Submitted
24 Nov. 2020
Accepted
18 Janv. 2021
First published
19 Janv. 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 2699-2715

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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