Half-sandwich Ru (II) complexes: Effect of ligands on aerobic oxidation of benzylamine

Ondřej Moždiak; Pooja Dubey; Libor Dostál; Zdena Růžičková; Jiří Tydlitát; Roman Jambor

doi:10.1002/aoc.7284

Half-sandwich Ru (II) complexes: Effect of ligands on aerobic oxidation of benzylamine

Ondřej Moždiak, Pooja Dubey, Libor Dostál, Zdena Růžičková, Jiří Tydlitát, Roman Jambor

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

Abstract

In this study, we compared carbene and pyridine substituted ligands {3-Me-1-[2-(CH₂CH₂SPh)]-C₇H₄N₂} (L¹) and {2-[(2,6-iPr₂-C₆H₃)N=CH]-6-(MeO)C₅H₃N}(L²) for synthesis of ionic C,S- and N,N-coordinated Ru (II) complexes [(κ²-L¹)RuCl(η⁶-p-cymene)]⁺Cl⁻ (1), [(κ²-L¹)RuI(η⁶-p-cymene)]⁺I⁻ (2), and [(κ²-L²)RuCl(η⁶-p-cymene)]⁺Cl⁻ (3), respectively. Stannylene ligand [{2,6-(Me₂NCH₂)₂C₆H₃}SnCl] (L³), as heavy carbene analog, was also used in this study to prepare neutral Sn-coordinated Ru (II) complex [(κ¹-L³)RuCl₂(η⁶-p-cymene)] (4). Finally, reaction of SnCl₂ with 1, 3, and 4 was also studied to yield [(κ²-L¹)RuCl(η⁶-p-cymene)]⁺[SnCl₃]⁻ (5), [(κ²-L²)RuCl(η⁶-p-cymene)]⁺[SnCl₃]⁻ (6), and [(κ¹-L³)RuCl (SnCl₃)(η⁶-p-cymene)] (7). The catalytic activity of 1–7 was tested on aerobic oxidation of benzylamine. The effect of different ligands L^1–3 as well as the effect of the SnCl₃⁻ moiety is discussed.

Original language	English
Article number	e7284
Journal	Applied Organometallic Chemistry
Volume	37
Issue number	12
DOIs	https://doi.org/10.1002/aoc.7284
State	Published - 1 Dec 2023
Externally published	Yes

Keywords

aerobic oxidation
bimetallic catalysts
chelating ligands
ruthenium

ASJC Scopus subject areas

General Chemistry
Inorganic Chemistry

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10.1002/aoc.7284

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title = "Half-sandwich Ru (II) complexes: Effect of ligands on aerobic oxidation of benzylamine",

abstract = "In this study, we compared carbene and pyridine substituted ligands {3-Me-1-[2-(CH2CH2SPh)]-C7H4N2} (L1) and {2-[(2,6-iPr2-C6H3)N=CH]-6-(MeO)C5H3N}(L2) for synthesis of ionic C,S- and N,N-coordinated Ru (II) complexes [(κ2-L1)RuCl(η6-p-cymene)]+Cl− (1), [(κ2-L1)RuI(η6-p-cymene)]+I− (2), and [(κ2-L2)RuCl(η6-p-cymene)]+Cl− (3), respectively. Stannylene ligand [{2,6-(Me2NCH2)2C6H3}SnCl] (L3), as heavy carbene analog, was also used in this study to prepare neutral Sn-coordinated Ru (II) complex [(κ1-L3)RuCl2(η6-p-cymene)] (4). Finally, reaction of SnCl2 with 1, 3, and 4 was also studied to yield [(κ2-L1)RuCl(η6-p-cymene)]+[SnCl3]− (5), [(κ2-L2)RuCl(η6-p-cymene)]+[SnCl3]− (6), and [(κ1-L3)RuCl (SnCl3)(η6-p-cymene)] (7). The catalytic activity of 1–7 was tested on aerobic oxidation of benzylamine. The effect of different ligands L1–3 as well as the effect of the SnCl3− moiety is discussed.",

keywords = "aerobic oxidation, bimetallic catalysts, chelating ligands, ruthenium",

author = "Ond{\v r}ej Mo{\v z}diak and Pooja Dubey and Libor Dost{\'a}l and Zdena Rů{\v z}i{\v c}kov{\'a} and Ji{\v r}{\'i} Tydlit{\'a}t and Roman Jambor",

note = "Publisher Copyright: {\textcopyright} 2023 John Wiley & Sons Ltd.",

year = "2023",

month = dec,

day = "1",

doi = "10.1002/aoc.7284",

language = "English",

volume = "37",

journal = "Applied Organometallic Chemistry",

issn = "0268-2605",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Half-sandwich Ru (II) complexes

T2 - Effect of ligands on aerobic oxidation of benzylamine

AU - Moždiak, Ondřej

AU - Dubey, Pooja

AU - Dostál, Libor

AU - Růžičková, Zdena

AU - Tydlitát, Jiří

AU - Jambor, Roman

PY - 2023/12/1

Y1 - 2023/12/1

N2 - In this study, we compared carbene and pyridine substituted ligands {3-Me-1-[2-(CH2CH2SPh)]-C7H4N2} (L1) and {2-[(2,6-iPr2-C6H3)N=CH]-6-(MeO)C5H3N}(L2) for synthesis of ionic C,S- and N,N-coordinated Ru (II) complexes [(κ2-L1)RuCl(η6-p-cymene)]+Cl− (1), [(κ2-L1)RuI(η6-p-cymene)]+I− (2), and [(κ2-L2)RuCl(η6-p-cymene)]+Cl− (3), respectively. Stannylene ligand [{2,6-(Me2NCH2)2C6H3}SnCl] (L3), as heavy carbene analog, was also used in this study to prepare neutral Sn-coordinated Ru (II) complex [(κ1-L3)RuCl2(η6-p-cymene)] (4). Finally, reaction of SnCl2 with 1, 3, and 4 was also studied to yield [(κ2-L1)RuCl(η6-p-cymene)]+[SnCl3]− (5), [(κ2-L2)RuCl(η6-p-cymene)]+[SnCl3]− (6), and [(κ1-L3)RuCl (SnCl3)(η6-p-cymene)] (7). The catalytic activity of 1–7 was tested on aerobic oxidation of benzylamine. The effect of different ligands L1–3 as well as the effect of the SnCl3− moiety is discussed.

AB - In this study, we compared carbene and pyridine substituted ligands {3-Me-1-[2-(CH2CH2SPh)]-C7H4N2} (L1) and {2-[(2,6-iPr2-C6H3)N=CH]-6-(MeO)C5H3N}(L2) for synthesis of ionic C,S- and N,N-coordinated Ru (II) complexes [(κ2-L1)RuCl(η6-p-cymene)]+Cl− (1), [(κ2-L1)RuI(η6-p-cymene)]+I− (2), and [(κ2-L2)RuCl(η6-p-cymene)]+Cl− (3), respectively. Stannylene ligand [{2,6-(Me2NCH2)2C6H3}SnCl] (L3), as heavy carbene analog, was also used in this study to prepare neutral Sn-coordinated Ru (II) complex [(κ1-L3)RuCl2(η6-p-cymene)] (4). Finally, reaction of SnCl2 with 1, 3, and 4 was also studied to yield [(κ2-L1)RuCl(η6-p-cymene)]+[SnCl3]− (5), [(κ2-L2)RuCl(η6-p-cymene)]+[SnCl3]− (6), and [(κ1-L3)RuCl (SnCl3)(η6-p-cymene)] (7). The catalytic activity of 1–7 was tested on aerobic oxidation of benzylamine. The effect of different ligands L1–3 as well as the effect of the SnCl3− moiety is discussed.

KW - aerobic oxidation

KW - bimetallic catalysts

KW - chelating ligands

KW - ruthenium

UR - http://www.scopus.com/inward/record.url?scp=85173977460&partnerID=8YFLogxK

U2 - 10.1002/aoc.7284

DO - 10.1002/aoc.7284

M3 - Article

AN - SCOPUS:85173977460

SN - 0268-2605

VL - 37

JO - Applied Organometallic Chemistry

JF - Applied Organometallic Chemistry

IS - 12

M1 - e7284

ER -

Half-sandwich Ru (II) complexes: Effect of ligands on aerobic oxidation of benzylamine

Abstract

Keywords

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