Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers': Via a zinc ion template-assisted synthesis

Thomas Simler; Andreas A. Danopoulos; Pierre Braunstein

doi:10.1039/c7dt01014a

Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers': Via a zinc ion template-assisted synthesis

Thomas Simler
, Andreas A. Danopoulos
, Pierre Braunstein

Université de Strasbourg

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

Abstract

New non-symmetrical, redox-active imino NHC pyridine pincer ligands, 2-(R¹-imidazol-2-ylidene)-6-(R²NCH)-pyridine (R¹ = 2,6-diisopropylphenyl (DiPP), R² = 2,4,6-trimethylphenyl (Mes), 4B; R¹ = R² = DiPP, 4C), have been accessed by a Zn^II-promoted modular synthesis involving the quaternization of R¹-imidazole by [Zn(κN^imineκN^pyridine)(2-(R²NCH)-6-bromo-pyridine)Cl₂], followed by Zn^II removal and deprotonation of imidazolium pro-ligands. Redox active forms of 4B were implicated in the two complexes obtained by its reaction with FeBr₂/KC₈; metrical data analysis pointed to the occurrence of radical anionic and dianionic redox states of 4B.

Original language	English
Pages (from-to)	5955-5964
Number of pages	10
Journal	Dalton Transactions
Volume	46
Issue number	18
DOIs	https://doi.org/10.1039/c7dt01014a
Publication status	Published - 1 Jan 2017
Externally published	Yes

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title = "Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers': Via a zinc ion template-assisted synthesis",

abstract = "New non-symmetrical, redox-active imino NHC pyridine pincer ligands, 2-(R1-imidazol-2-ylidene)-6-(R2NCH)-pyridine (R1 = 2,6-diisopropylphenyl (DiPP), R2 = 2,4,6-trimethylphenyl (Mes), 4B; R1 = R2 = DiPP, 4C), have been accessed by a ZnII-promoted modular synthesis involving the quaternization of R1-imidazole by [Zn(κNimineκNpyridine)(2-(R2NCH)-6-bromo-pyridine)Cl2], followed by ZnII removal and deprotonation of imidazolium pro-ligands. Redox active forms of 4B were implicated in the two complexes obtained by its reaction with FeBr2/KC8; metrical data analysis pointed to the occurrence of radical anionic and dianionic redox states of 4B.",

author = "Thomas Simler and Danopoulos, \{Andreas A.\} and Pierre Braunstein",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2017.",

year = "2017",

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day = "1",

doi = "10.1039/c7dt01014a",

language = "English",

volume = "46",

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journal = "Dalton Transactions",

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TY - JOUR

T1 - Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers'

T2 - Via a zinc ion template-assisted synthesis

AU - Simler, Thomas

AU - Danopoulos, Andreas A.

AU - Braunstein, Pierre

N1 - Publisher Copyright: © The Royal Society of Chemistry 2017.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - New non-symmetrical, redox-active imino NHC pyridine pincer ligands, 2-(R1-imidazol-2-ylidene)-6-(R2NCH)-pyridine (R1 = 2,6-diisopropylphenyl (DiPP), R2 = 2,4,6-trimethylphenyl (Mes), 4B; R1 = R2 = DiPP, 4C), have been accessed by a ZnII-promoted modular synthesis involving the quaternization of R1-imidazole by [Zn(κNimineκNpyridine)(2-(R2NCH)-6-bromo-pyridine)Cl2], followed by ZnII removal and deprotonation of imidazolium pro-ligands. Redox active forms of 4B were implicated in the two complexes obtained by its reaction with FeBr2/KC8; metrical data analysis pointed to the occurrence of radical anionic and dianionic redox states of 4B.

AB - New non-symmetrical, redox-active imino NHC pyridine pincer ligands, 2-(R1-imidazol-2-ylidene)-6-(R2NCH)-pyridine (R1 = 2,6-diisopropylphenyl (DiPP), R2 = 2,4,6-trimethylphenyl (Mes), 4B; R1 = R2 = DiPP, 4C), have been accessed by a ZnII-promoted modular synthesis involving the quaternization of R1-imidazole by [Zn(κNimineκNpyridine)(2-(R2NCH)-6-bromo-pyridine)Cl2], followed by ZnII removal and deprotonation of imidazolium pro-ligands. Redox active forms of 4B were implicated in the two complexes obtained by its reaction with FeBr2/KC8; metrical data analysis pointed to the occurrence of radical anionic and dianionic redox states of 4B.

UR - https://www.scopus.com/pages/publications/85021732900

U2 - 10.1039/c7dt01014a

DO - 10.1039/c7dt01014a

M3 - Article

C2 - 28418439

AN - SCOPUS:85021732900

SN - 1477-9226

VL - 46

SP - 5955

EP - 5964

JO - Dalton Transactions

JF - Dalton Transactions

IS - 18

ER -

Non-symmetrical, potentially redox non-innocent imino NHC pyridine 'pincers': Via a zinc ion template-assisted synthesis

Abstract

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