Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Pierre Queval; Claire Jahier; Mathieu Rouen; Isabelle Artur; Jean Christophe Legeay; Laura Falivene; Loïc J. Toupet; Christophe Crévisy; Luigi Cavallo; Olivier Baslé; Marc Mauduit

doi:10.1002/anie.201308873

Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Pierre Queval, Claire Jahier, Mathieu Rouen, Isabelle Artur, Jean Christophe Legeay, Laura Falivene, Loïc J. Toupet, Christophe Crévisy, Luigi Cavallo, Olivier Baslé, Marc Mauduit

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

63 Scopus citations

Abstract

A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	14103-14107
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	52
Issue number	52
DOIs	https://doi.org/10.1002/anie.201308873
State	Published - Dec 4 2013

ASJC Scopus subject areas

Chemistry(all)
Catalysis

Access to Document

10.1002/anie.201308873

Cite this

Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J. C., Falivene, L., Toupet, L. J., Crévisy, C., Cavallo, L., Baslé, O., & Mauduit, M. (2013). Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes. Angewandte Chemie International Edition, 52(52), 14103-14107. https://doi.org/10.1002/anie.201308873

@article{360be8b8e96b4f79b8e27a4cf68e1726,

title = "Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes",

abstract = "A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Pierre Queval and Claire Jahier and Mathieu Rouen and Isabelle Artur and Legeay, {Jean Christophe} and Laura Falivene and Toupet, {Lo{\"i}c J.} and Christophe Cr{\'e}visy and Luigi Cavallo and Olivier Basl{\'e} and Marc Mauduit",

note = "KAUST Repository Item: Exported on 2020-10-01",

year = "2013",

month = dec,

day = "4",

doi = "10.1002/anie.201308873",

language = "English (US)",

volume = "52",

pages = "14103--14107",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "52",

}

Queval, P, Jahier, C, Rouen, M, Artur, I, Legeay, JC, Falivene, L, Toupet, LJ, Crévisy, C, Cavallo, L, Baslé, O & Mauduit, M 2013, 'Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes', Angewandte Chemie International Edition, vol. 52, no. 52, pp. 14103-14107. https://doi.org/10.1002/anie.201308873

TY - JOUR

T1 - Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

AU - Queval, Pierre

AU - Jahier, Claire

AU - Rouen, Mathieu

AU - Artur, Isabelle

AU - Legeay, Jean Christophe

AU - Falivene, Laura

AU - Toupet, Loïc J.

AU - Crévisy, Christophe

AU - Cavallo, Luigi

AU - Baslé, Olivier

AU - Mauduit, Marc

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2013/12/4

Y1 - 2013/12/4

N2 - A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/563141

UR - http://doi.wiley.com/10.1002/anie.201308873

UR - http://www.scopus.com/inward/record.url?scp=84890640557&partnerID=8YFLogxK

U2 - 10.1002/anie.201308873

DO - 10.1002/anie.201308873

M3 - Article

SN - 1433-7851

VL - 52

SP - 14103

EP - 14107

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 52

ER -

Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 933273: Experimental Crystal Structure Determination : Chloro-(1-cyclododecyl-3-mesitylimidazol-2-ylidene)-gold

CCDC 933067: Experimental Crystal Structure Determination : Dicarbonyl-chloro-(1-cycloheptyl-3-mesitylimidazol-2-ylidene)-iridium

CCDC 904639: Experimental Crystal Structure Determination : 3-Cyclopentyl-1-mesityl-1H-imidazol-3-ium tetrafluoroborate

Cite this

Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 933273: Experimental Crystal Structure Determination : Chloro-(1-cyclododecyl-3-mesitylimidazol-2-ylidene)-gold

CCDC 933067: Experimental Crystal Structure Determination : Dicarbonyl-chloro-(1-cycloheptyl-3-mesitylimidazol-2-ylidene)-iridium

CCDC 904639: Experimental Crystal Structure Determination : 3-Cyclopentyl-1-mesityl-1H-imidazol-3-ium tetrafluoroborate

Cite this