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Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization
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| Zeitschriftentitel: | Applied Organometallic Chemistry |
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| Personen und Körperschaften: | , , , , |
| In: | Applied Organometallic Chemistry, 34, 2020, 1 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie |
|---|---|
| author |
Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie |
| spellingShingle |
Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie Applied Organometallic Chemistry Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization Inorganic Chemistry General Chemistry |
| author_sort |
li, min |
| spelling |
Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie 0268-2605 1099-0739 Wiley Inorganic Chemistry General Chemistry http://dx.doi.org/10.1002/aoc.5296 <jats:p>A library of rare‐earth metal derivatives supported by an aminophenoxy ligand was prepared and their catalytic performance in lactide polymerization was investigated. It was found that the synthetic strategy had a profound effect on the formation of aminophenoxy rare‐earth metal complexes. Amine elimination between Ln[N(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]<jats:sub>3</jats:sub>(μ‐Cl)Li(THF)<jats:sub>3</jats:sub> (Ln = Yb, Y) and 1 equiv. of the aminophenol [HONH] ([HONH] = <jats:italic>ο</jats:italic>‐OCH<jats:sub>3</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NHCH<jats:sub>2</jats:sub>(3,5‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu<jats:sub>2</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>2</jats:sub>‐2‐OH)) in toluene gave the unexpected heterobimetallic bis(aminophenoxy) rare‐earth metal complexes [ON]<jats:sub>2</jats:sub>LnLi(THF)<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>1</jats:bold>), Y (<jats:bold>2</jats:bold>)). When the reactions were carried out in THF and TMEDA, amine elimination produced the aminophenoxy rare‐earth metal amide complexes {[ON]LnN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>5</jats:bold>), Y (<jats:bold>6</jats:bold>)) in <jats:italic>ca</jats:italic> 85% isolated yields. Complexes <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold> could also be obtained from salt metathesis reaction of {[ON]LnCl(THF)}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>3</jats:bold>), Y (<jats:bold>4</jats:bold>)) with NaN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub> in a 1:2 molar ratio. In addition, treatment of complexes <jats:bold>3</jats:bold> and <jats:bold>4</jats:bold> with NaOAr (Ar = &bond;C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>‐4‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu) and (SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>NC(NPr<jats:sup><jats:italic>i</jats:italic></jats:sup>)<jats:sub>2</jats:sub>Na in 1:4 and 1:2 molar ratios provided the corresponding aminophenoxy rare‐earth metal derivatives {[ON](μ‐OAr)Ln(μ‐OAr)Na(THF)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>7</jats:bold>), Y (<jats:bold>8</jats:bold>)) and {[ON]Ln[(<jats:sup><jats:italic>i</jats:italic></jats:sup>PrN)<jats:sub>2</jats:sub>CN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>9</jats:bold>), Y (<jats:bold>10</jats:bold>)), respectively. These complexes were fully characterized, and their molecular structures were determined using single‐crystal X‐ray diffraction. Polymerization experiments showed that complexes <jats:bold>1</jats:bold>, <jats:bold>2</jats:bold>, <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> were highly active for the ring‐opening polymerization of <jats:sc>l</jats:sc>‐lactide in toluene, and complex <jats:bold>1</jats:bold> promoted <jats:sc>l</jats:sc>‐lactide polymerization in a controlled fashion. The polymerization of <jats:italic>rac</jats:italic>‐lactide initiated by the neutral aminophenoxy rare‐earth metal complexes <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> in THF afforded heterotactic polymers.</jats:p> Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization Applied Organometallic Chemistry |
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10.1002/aoc.5296 |
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Chemie und Pharmazie |
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Wiley, 2020 |
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li2020rareearthmetalderivativessupportedbyaminophenoxyligandsynthesischaracterizationandcatalyticperformanceinlactidepolymerization |
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2020 |
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Wiley |
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Applied Organometallic Chemistry |
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49 |
| title |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_unstemmed |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_full |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_fullStr |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_full_unstemmed |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_short |
Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_sort |
rare‐earth metal derivatives supported by aminophenoxy ligand: synthesis, characterization and catalytic performance in lactide polymerization |
| topic |
Inorganic Chemistry General Chemistry |
| url |
http://dx.doi.org/10.1002/aoc.5296 |
| publishDate |
2020 |
| physical |
|
| description |
<jats:p>A library of rare‐earth metal derivatives supported by an aminophenoxy ligand was prepared and their catalytic performance in lactide polymerization was investigated. It was found that the synthetic strategy had a profound effect on the formation of aminophenoxy rare‐earth metal complexes. Amine elimination between Ln[N(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]<jats:sub>3</jats:sub>(μ‐Cl)Li(THF)<jats:sub>3</jats:sub> (Ln = Yb, Y) and 1 equiv. of the aminophenol [HONH] ([HONH] = <jats:italic>ο</jats:italic>‐OCH<jats:sub>3</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NHCH<jats:sub>2</jats:sub>(3,5‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu<jats:sub>2</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>2</jats:sub>‐2‐OH)) in toluene gave the unexpected heterobimetallic bis(aminophenoxy) rare‐earth metal complexes [ON]<jats:sub>2</jats:sub>LnLi(THF)<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>1</jats:bold>), Y (<jats:bold>2</jats:bold>)). When the reactions were carried out in THF and TMEDA, amine elimination produced the aminophenoxy rare‐earth metal amide complexes {[ON]LnN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>5</jats:bold>), Y (<jats:bold>6</jats:bold>)) in <jats:italic>ca</jats:italic> 85% isolated yields. Complexes <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold> could also be obtained from salt metathesis reaction of {[ON]LnCl(THF)}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>3</jats:bold>), Y (<jats:bold>4</jats:bold>)) with NaN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub> in a 1:2 molar ratio. In addition, treatment of complexes <jats:bold>3</jats:bold> and <jats:bold>4</jats:bold> with NaOAr (Ar = &bond;C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>‐4‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu) and (SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>NC(NPr<jats:sup><jats:italic>i</jats:italic></jats:sup>)<jats:sub>2</jats:sub>Na in 1:4 and 1:2 molar ratios provided the corresponding aminophenoxy rare‐earth metal derivatives {[ON](μ‐OAr)Ln(μ‐OAr)Na(THF)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>7</jats:bold>), Y (<jats:bold>8</jats:bold>)) and {[ON]Ln[(<jats:sup><jats:italic>i</jats:italic></jats:sup>PrN)<jats:sub>2</jats:sub>CN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>9</jats:bold>), Y (<jats:bold>10</jats:bold>)), respectively. These complexes were fully characterized, and their molecular structures were determined using single‐crystal X‐ray diffraction. Polymerization experiments showed that complexes <jats:bold>1</jats:bold>, <jats:bold>2</jats:bold>, <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> were highly active for the ring‐opening polymerization of <jats:sc>l</jats:sc>‐lactide in toluene, and complex <jats:bold>1</jats:bold> promoted <jats:sc>l</jats:sc>‐lactide polymerization in a controlled fashion. The polymerization of <jats:italic>rac</jats:italic>‐lactide initiated by the neutral aminophenoxy rare‐earth metal complexes <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> in THF afforded heterotactic polymers.</jats:p> |
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| author | Li, Min, Zhang, Jie, Chen, Jue, Yao, Yingming, Luo, Yunjie |
| author_facet | Li, Min, Zhang, Jie, Chen, Jue, Yao, Yingming, Luo, Yunjie, Li, Min, Zhang, Jie, Chen, Jue, Yao, Yingming, Luo, Yunjie |
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| description | <jats:p>A library of rare‐earth metal derivatives supported by an aminophenoxy ligand was prepared and their catalytic performance in lactide polymerization was investigated. It was found that the synthetic strategy had a profound effect on the formation of aminophenoxy rare‐earth metal complexes. Amine elimination between Ln[N(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]<jats:sub>3</jats:sub>(μ‐Cl)Li(THF)<jats:sub>3</jats:sub> (Ln = Yb, Y) and 1 equiv. of the aminophenol [HONH] ([HONH] = <jats:italic>ο</jats:italic>‐OCH<jats:sub>3</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NHCH<jats:sub>2</jats:sub>(3,5‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu<jats:sub>2</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>2</jats:sub>‐2‐OH)) in toluene gave the unexpected heterobimetallic bis(aminophenoxy) rare‐earth metal complexes [ON]<jats:sub>2</jats:sub>LnLi(THF)<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>1</jats:bold>), Y (<jats:bold>2</jats:bold>)). When the reactions were carried out in THF and TMEDA, amine elimination produced the aminophenoxy rare‐earth metal amide complexes {[ON]LnN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>5</jats:bold>), Y (<jats:bold>6</jats:bold>)) in <jats:italic>ca</jats:italic> 85% isolated yields. Complexes <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold> could also be obtained from salt metathesis reaction of {[ON]LnCl(THF)}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>3</jats:bold>), Y (<jats:bold>4</jats:bold>)) with NaN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub> in a 1:2 molar ratio. In addition, treatment of complexes <jats:bold>3</jats:bold> and <jats:bold>4</jats:bold> with NaOAr (Ar = &bond;C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>‐4‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu) and (SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>NC(NPr<jats:sup><jats:italic>i</jats:italic></jats:sup>)<jats:sub>2</jats:sub>Na in 1:4 and 1:2 molar ratios provided the corresponding aminophenoxy rare‐earth metal derivatives {[ON](μ‐OAr)Ln(μ‐OAr)Na(THF)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>7</jats:bold>), Y (<jats:bold>8</jats:bold>)) and {[ON]Ln[(<jats:sup><jats:italic>i</jats:italic></jats:sup>PrN)<jats:sub>2</jats:sub>CN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>9</jats:bold>), Y (<jats:bold>10</jats:bold>)), respectively. These complexes were fully characterized, and their molecular structures were determined using single‐crystal X‐ray diffraction. Polymerization experiments showed that complexes <jats:bold>1</jats:bold>, <jats:bold>2</jats:bold>, <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> were highly active for the ring‐opening polymerization of <jats:sc>l</jats:sc>‐lactide in toluene, and complex <jats:bold>1</jats:bold> promoted <jats:sc>l</jats:sc>‐lactide polymerization in a controlled fashion. The polymerization of <jats:italic>rac</jats:italic>‐lactide initiated by the neutral aminophenoxy rare‐earth metal complexes <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> in THF afforded heterotactic polymers.</jats:p> |
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| imprint | Wiley, 2020 |
| imprint_str_mv | Wiley, 2020 |
| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| spelling | Li, Min Zhang, Jie Chen, Jue Yao, Yingming Luo, Yunjie 0268-2605 1099-0739 Wiley Inorganic Chemistry General Chemistry http://dx.doi.org/10.1002/aoc.5296 <jats:p>A library of rare‐earth metal derivatives supported by an aminophenoxy ligand was prepared and their catalytic performance in lactide polymerization was investigated. It was found that the synthetic strategy had a profound effect on the formation of aminophenoxy rare‐earth metal complexes. Amine elimination between Ln[N(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]<jats:sub>3</jats:sub>(μ‐Cl)Li(THF)<jats:sub>3</jats:sub> (Ln = Yb, Y) and 1 equiv. of the aminophenol [HONH] ([HONH] = <jats:italic>ο</jats:italic>‐OCH<jats:sub>3</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NHCH<jats:sub>2</jats:sub>(3,5‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu<jats:sub>2</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>2</jats:sub>‐2‐OH)) in toluene gave the unexpected heterobimetallic bis(aminophenoxy) rare‐earth metal complexes [ON]<jats:sub>2</jats:sub>LnLi(THF)<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>1</jats:bold>), Y (<jats:bold>2</jats:bold>)). When the reactions were carried out in THF and TMEDA, amine elimination produced the aminophenoxy rare‐earth metal amide complexes {[ON]LnN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>5</jats:bold>), Y (<jats:bold>6</jats:bold>)) in <jats:italic>ca</jats:italic> 85% isolated yields. Complexes <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold> could also be obtained from salt metathesis reaction of {[ON]LnCl(THF)}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>3</jats:bold>), Y (<jats:bold>4</jats:bold>)) with NaN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub> in a 1:2 molar ratio. In addition, treatment of complexes <jats:bold>3</jats:bold> and <jats:bold>4</jats:bold> with NaOAr (Ar = &bond;C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>‐4‐<jats:sup><jats:italic>t</jats:italic></jats:sup>Bu) and (SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>NC(NPr<jats:sup><jats:italic>i</jats:italic></jats:sup>)<jats:sub>2</jats:sub>Na in 1:4 and 1:2 molar ratios provided the corresponding aminophenoxy rare‐earth metal derivatives {[ON](μ‐OAr)Ln(μ‐OAr)Na(THF)<jats:sub>2</jats:sub>}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>7</jats:bold>), Y (<jats:bold>8</jats:bold>)) and {[ON]Ln[(<jats:sup><jats:italic>i</jats:italic></jats:sup>PrN)<jats:sub>2</jats:sub>CN(SiMe<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>]}<jats:sub>2</jats:sub> (Ln = Yb (<jats:bold>9</jats:bold>), Y (<jats:bold>10</jats:bold>)), respectively. These complexes were fully characterized, and their molecular structures were determined using single‐crystal X‐ray diffraction. Polymerization experiments showed that complexes <jats:bold>1</jats:bold>, <jats:bold>2</jats:bold>, <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> were highly active for the ring‐opening polymerization of <jats:sc>l</jats:sc>‐lactide in toluene, and complex <jats:bold>1</jats:bold> promoted <jats:sc>l</jats:sc>‐lactide polymerization in a controlled fashion. The polymerization of <jats:italic>rac</jats:italic>‐lactide initiated by the neutral aminophenoxy rare‐earth metal complexes <jats:bold>5</jats:bold>, <jats:bold>6</jats:bold>, <jats:bold>9</jats:bold> and <jats:bold>10</jats:bold> in THF afforded heterotactic polymers.</jats:p> Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization Applied Organometallic Chemistry |
| spellingShingle | Li, Min, Zhang, Jie, Chen, Jue, Yao, Yingming, Luo, Yunjie, Applied Organometallic Chemistry, Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization, Inorganic Chemistry, General Chemistry |
| title | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_full | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_fullStr | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_full_unstemmed | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_short | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| title_sort | rare‐earth metal derivatives supported by aminophenoxy ligand: synthesis, characterization and catalytic performance in lactide polymerization |
| title_unstemmed | Rare‐earth metal derivatives supported by aminophenoxy ligand: Synthesis, characterization and catalytic performance in lactide polymerization |
| topic | Inorganic Chemistry, General Chemistry |
| url | http://dx.doi.org/10.1002/aoc.5296 |