EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes

Huanhuan Dong; Albert Martinez-Segura; Riley W. Kelehan; Connor Bourne; Aidan McKay; Alexandra Martha Zoya Slawin; David Bradford Cordes; Andreas Stasch

doi:10.3390/inorganics13010027

^EtIDip (^EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes

Huanhuan Dong, Albert Martinez-Segura, Riley W. Kelehan, Connor Bourne, Aidan McKay, Alexandra Martha Zoya Slawin, David Bradford Cordes, Andreas Stasch^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene ^EtIDip (^EtIPr), {EtCN(Dip)}₂C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}₂C:. The N-heterocyclic carbene ^EtIDip could be further converted to the oxidised species [^EtIDipCl]Cl, ^EtIDipF₂, ^EtIDipO, and ^EtIDipSe, and the group 13 element complexes ^EtIDipEX₃, with E = B, X = Br; E = Al, X = I; E = Ga, X = I; E = Al, X = H. The properties of the ^EtIDip and IDip ligands are compared and the molecular structures of (DipNCEt)₂, [^EtIDipH]Cl, [^EtIDipH]I, ^EtIDip, [^EtIDipCl]Cl, ^EtIDipF₂, ^EtIDipO, ^EtIDipBBr₃, ^EtIDipAlI₃, ^EtIDipGaI₃, and ^EtIDipAlH₃ have been determined.

Original language	English
Article number	27
Number of pages	24
Journal	Inorganics
Volume	13
Issue number	1
DOIs	https://doi.org/10.3390/inorganics13010027
Publication status	Published - 17 Jan 2025

Keywords

Group 13 complexes
Hydrides
N-heterocyclic carbenes
Stable carbenes
Sterically demanding ligands

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10.3390/inorganics13010027Licence: CC BY

Dong-2025-Inorganics-13-00027-CCBY
Copyright: © 2025 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
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EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes (dataset)
Dong, H. (Creator), Martinez-Segura, A. (Creator), Kelehan, R. W. (Creator), Bourne, C. (Creator), McKay, A. (Creator), Slawin, A. M. Z. (Creator), Cordes, D. B. (Creator) & Stasch, A. (Creator), University of St Andrews, 25 Jan 2025
DOI: 10.17630/4fff14ab-7f00-47e4-a5ae-990402460aa2
Dataset

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Ligand variations in low oxidation state group 13 and group 14 compounds: synthesis, characterisation, and novel reactivity
Dong, H. (Author), Stasch, A. (Supervisor), 3 Dec 2025
Student thesis: Doctoral Thesis (PhD)

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title = "EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes",

abstract = "We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene EtIDip (EtIPr), {EtCN(Dip)}2C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}2C:. The N-heterocyclic carbene EtIDip could be further converted to the oxidised species [EtIDipCl]Cl, EtIDipF2, EtIDipO, and EtIDipSe, and the group 13 element complexes EtIDipEX3, with E = B, X = Br; E = Al, X = I; E = Ga, X = I; E = Al, X = H. The properties of the EtIDip and IDip ligands are compared and the molecular structures of (DipNCEt)2, [EtIDipH]Cl, [EtIDipH]I, EtIDip, [EtIDipCl]Cl, EtIDipF2, EtIDipO, EtIDipBBr3, EtIDipAlI3, EtIDipGaI3, and EtIDipAlH3 have been determined.",

keywords = "Group 13 complexes, Hydrides, N-heterocyclic carbenes, Stable carbenes, Sterically demanding ligands",

author = "Huanhuan Dong and Albert Martinez-Segura and Kelehan, {Riley W.} and Connor Bourne and Aidan McKay and Slawin, {Alexandra Martha Zoya} and Cordes, {David Bradford} and Andreas Stasch",

note = "Funding: We are grateful to the China Scholarship Council (H.D.), the EPSRC DTG (EP/R513337/1) (C.B.), Erasmus+ (A.M.-S.), and the School of Chemistry at the University of St Andrews for support.",

year = "2025",

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doi = "10.3390/inorganics13010027",

language = "English",

volume = "13",

journal = "Inorganics",

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publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

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T1 - EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes

AU - Dong, Huanhuan

AU - Martinez-Segura, Albert

AU - Kelehan, Riley W.

AU - Bourne, Connor

AU - McKay, Aidan

AU - Slawin, Alexandra Martha Zoya

AU - Cordes, David Bradford

AU - Stasch, Andreas

N1 - Funding: We are grateful to the China Scholarship Council (H.D.), the EPSRC DTG (EP/R513337/1) (C.B.), Erasmus+ (A.M.-S.), and the School of Chemistry at the University of St Andrews for support.

PY - 2025/1/17

Y1 - 2025/1/17

N2 - We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene EtIDip (EtIPr), {EtCN(Dip)}2C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}2C:. The N-heterocyclic carbene EtIDip could be further converted to the oxidised species [EtIDipCl]Cl, EtIDipF2, EtIDipO, and EtIDipSe, and the group 13 element complexes EtIDipEX3, with E = B, X = Br; E = Al, X = I; E = Ga, X = I; E = Al, X = H. The properties of the EtIDip and IDip ligands are compared and the molecular structures of (DipNCEt)2, [EtIDipH]Cl, [EtIDipH]I, EtIDip, [EtIDipCl]Cl, EtIDipF2, EtIDipO, EtIDipBBr3, EtIDipAlI3, EtIDipGaI3, and EtIDipAlH3 have been determined.

AB - We report the synthesis, characterisation and reactivity of the stable imidazol-2-ylidene EtIDip (EtIPr), {EtCN(Dip)}2C:, Dip = 2,6-iPr2C6H3, as a chemically robust alternative to IDip (IPr), {HCN(Dip)}2C:. The N-heterocyclic carbene EtIDip could be further converted to the oxidised species [EtIDipCl]Cl, EtIDipF2, EtIDipO, and EtIDipSe, and the group 13 element complexes EtIDipEX3, with E = B, X = Br; E = Al, X = I; E = Ga, X = I; E = Al, X = H. The properties of the EtIDip and IDip ligands are compared and the molecular structures of (DipNCEt)2, [EtIDipH]Cl, [EtIDipH]I, EtIDip, [EtIDipCl]Cl, EtIDipF2, EtIDipO, EtIDipBBr3, EtIDipAlI3, EtIDipGaI3, and EtIDipAlH3 have been determined.

KW - Group 13 complexes

KW - Hydrides

KW - N-heterocyclic carbenes

KW - Stable carbenes

KW - Sterically demanding ligands

U2 - 10.3390/inorganics13010027

DO - 10.3390/inorganics13010027

M3 - Article

SN - 2304-6740

VL - 13

JO - Inorganics

JF - Inorganics

IS - 1

M1 - 27

ER -

EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes

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EtIDip (EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes (dataset)

Student theses

Ligand variations in low oxidation state group 13 and group 14 compounds: synthesis, characterisation, and novel reactivity

Cite this

^EtIDip (^EtIPr) – Synthesis, characterisation and reactivity of a robust, backbone-modified N-heterocyclic carbene and group 13 element complexes