Ruthenium-Catalyzed Oxidative Homocoupling of Arylboronic Acids in Water : Ligand Tuned Reactivity and Mechanistic Study
Molecular catalysts based on water-soluble arene-Ru(II) complexes ([Ru]-1-[Ru]-5) containing aniline (L1), 2-methylaniline (L2), 2,6-dimethylaniline (L3), 4-methylaniline (L4), and 4-chloroaniline (L5) were designed for the homocoupling of arylboronic acids in water. These complexes were fully characterized by (1)H, (13)C NMR, mass spectrometry, and elemental analyses. Structural geometry for two of the representative arene-Ru(II) complexes [Ru]-3 and [Ru]-4 was established by single-crystal X-ray diffraction studies. Our studies showed that the selectivity toward biaryls products is influenced by the position and the electronic behavior of various substituents of aniline ligand coordinated to ruthenium. Extensive investigations using (1)H NMR, (19)F NMR, and mass spectral studies provided insights into the mechanistic pathway of homocoupling of arylboronic acids, where the identification of important organometallic intermediates, such as σ-aryl/di(σ-aryl) coordinated arene-Ru(II) species, suggested that the reaction proceeds through the formation of crucial di(σ-aryl)-Ru intermediates by the interaction of arylboronic acid with Ru-catalyst to yield biaryl products.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2016 |
|---|---|
| Erschienen: |
2016 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:55 |
|---|---|
| Enthalten in: |
Inorganic chemistry - 55(2016), 12 vom: 20. Juni, Seite 6332-43 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Tyagi, Deepika [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Completed 16.01.2018 Date Revised 16.01.2018 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.inorgchem.6b01115 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM261182935 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM261182935 | ||
| 003 | DE-627 | ||
| 005 | 20231224195014.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231224s2016 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.inorgchem.6b01115 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n0870.xml |
| 035 | |a (DE-627)NLM261182935 | ||
| 035 | |a (NLM)27276384 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Tyagi, Deepika |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Ruthenium-Catalyzed Oxidative Homocoupling of Arylboronic Acids in Water |b Ligand Tuned Reactivity and Mechanistic Study |
| 264 | 1 | |c 2016 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 16.01.2018 | ||
| 500 | |a Date Revised 16.01.2018 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Molecular catalysts based on water-soluble arene-Ru(II) complexes ([Ru]-1-[Ru]-5) containing aniline (L1), 2-methylaniline (L2), 2,6-dimethylaniline (L3), 4-methylaniline (L4), and 4-chloroaniline (L5) were designed for the homocoupling of arylboronic acids in water. These complexes were fully characterized by (1)H, (13)C NMR, mass spectrometry, and elemental analyses. Structural geometry for two of the representative arene-Ru(II) complexes [Ru]-3 and [Ru]-4 was established by single-crystal X-ray diffraction studies. Our studies showed that the selectivity toward biaryls products is influenced by the position and the electronic behavior of various substituents of aniline ligand coordinated to ruthenium. Extensive investigations using (1)H NMR, (19)F NMR, and mass spectral studies provided insights into the mechanistic pathway of homocoupling of arylboronic acids, where the identification of important organometallic intermediates, such as σ-aryl/di(σ-aryl) coordinated arene-Ru(II) species, suggested that the reaction proceeds through the formation of crucial di(σ-aryl)-Ru intermediates by the interaction of arylboronic acid with Ru-catalyst to yield biaryl products | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Binnani, Chinky |e verfasserin |4 aut | |
| 700 | 1 | |a Rai, Rohit K |e verfasserin |4 aut | |
| 700 | 1 | |a Dwivedi, Ambikesh D |e verfasserin |4 aut | |
| 700 | 1 | |a Gupta, Kavita |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Pei-Zhou |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Yanli |e verfasserin |4 aut | |
| 700 | 1 | |a Singh, Sanjay K |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Inorganic chemistry |d 1966 |g 55(2016), 12 vom: 20. Juni, Seite 6332-43 |w (DE-627)NLM110650298 |x 1520-510X |7 nnns |
| 773 | 1 | 8 | |g volume:55 |g year:2016 |g number:12 |g day:20 |g month:06 |g pages:6332-43 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.inorgchem.6b01115 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 55 |j 2016 |e 12 |b 20 |c 06 |h 6332-43 | ||