Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex
Reactions of isocyanates/isothiocyanates with primary and secondary phosphines without solvent at room temperature afforded phosphinecarboxamide/phosphinecarbothioamide, respectively, in excellent yields. Furthermore, palladium complex Pd(COD)Cl<sub>2</sub> was allowed to react with Ph&l...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5564 |
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| author | Masumi Itazaki Kento Okabayashi Takanari Matsutani Tomoya Nochida Toshiyuki Moriuchi Hiroshi Nakazawa |
| author_facet | Masumi Itazaki Kento Okabayashi Takanari Matsutani Tomoya Nochida Toshiyuki Moriuchi Hiroshi Nakazawa |
| author_sort | Masumi Itazaki |
| collection | DOAJ |
| description | Reactions of isocyanates/isothiocyanates with primary and secondary phosphines without solvent at room temperature afforded phosphinecarboxamide/phosphinecarbothioamide, respectively, in excellent yields. Furthermore, palladium complex Pd(COD)Cl<sub>2</sub> was allowed to react with Ph<sub>2</sub>PC(O)NHPh (<b>1a</b>) to afford [Pd{Ph<sub>2</sub>PC(O)NHPh-κ<i>P</i>}<sub>2</sub>Cl<sub>2</sub>] (<b>3</b>). On the other hand, the reaction of Pd(COD)Cl<sub>2</sub> with 1 eq. of Ph<sub>2</sub>PC(S)NHPh (<b>2a</b>) afforded [PdCl<sub>2</sub>{Ph<sub>2</sub>PC(S)NHPh-κ<i>P,S</i>}] (<b>4</b>). In the case of a 1:2 molar ratio, [PdCl{Ph<sub>2</sub>PC(S)NHPh-κ<i>P,S</i>}{Ph<sub>2</sub>PC(S)NHPh-κ<i>P</i>}]Cl (<b>5</b>) was formed. The newly obtained compounds were fully characterized using multielement NMR measurements and elemental analyses. In addition, the molecular structures of Ph<sub>2</sub>PC(O)NH(CH<sub>2</sub>)<sub>2</sub>Cl (<b>1j</b>), Ph<sub>2</sub>PC(S)NHPh(4-Cl) (<b>2c</b>), and <b>3</b>–<b>5</b> were determined using single-crystal X-ray diffraction. |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:30:12Z |
| publishDate | 2022-08-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f2689e7e024a4e92b82e844cd29081112023-11-23T13:44:11ZengMDPI AGMolecules1420-30492022-08-012717556410.3390/molecules27175564Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) ComplexMasumi Itazaki0Kento Okabayashi1Takanari Matsutani2Tomoya Nochida3Toshiyuki Moriuchi4Hiroshi Nakazawa5Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, Sumiyoshi-ku, Osaka 558-8585, JapanDepartment of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, JapanDepartment of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, JapanDepartment of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, JapanDepartment of Chemistry, Graduate School of Science, Osaka Metropolitan University, Sumiyoshi-ku, Osaka 558-8585, JapanDepartment of Chemistry, Graduate School of Science, Osaka Metropolitan University, Sumiyoshi-ku, Osaka 558-8585, JapanReactions of isocyanates/isothiocyanates with primary and secondary phosphines without solvent at room temperature afforded phosphinecarboxamide/phosphinecarbothioamide, respectively, in excellent yields. Furthermore, palladium complex Pd(COD)Cl<sub>2</sub> was allowed to react with Ph<sub>2</sub>PC(O)NHPh (<b>1a</b>) to afford [Pd{Ph<sub>2</sub>PC(O)NHPh-κ<i>P</i>}<sub>2</sub>Cl<sub>2</sub>] (<b>3</b>). On the other hand, the reaction of Pd(COD)Cl<sub>2</sub> with 1 eq. of Ph<sub>2</sub>PC(S)NHPh (<b>2a</b>) afforded [PdCl<sub>2</sub>{Ph<sub>2</sub>PC(S)NHPh-κ<i>P,S</i>}] (<b>4</b>). In the case of a 1:2 molar ratio, [PdCl{Ph<sub>2</sub>PC(S)NHPh-κ<i>P,S</i>}{Ph<sub>2</sub>PC(S)NHPh-κ<i>P</i>}]Cl (<b>5</b>) was formed. The newly obtained compounds were fully characterized using multielement NMR measurements and elemental analyses. In addition, the molecular structures of Ph<sub>2</sub>PC(O)NH(CH<sub>2</sub>)<sub>2</sub>Cl (<b>1j</b>), Ph<sub>2</sub>PC(S)NHPh(4-Cl) (<b>2c</b>), and <b>3</b>–<b>5</b> were determined using single-crystal X-ray diffraction.https://www.mdpi.com/1420-3049/27/17/5564hydrophosphinationphosphinecarboxamidephosphinecarbothioamidepalladium(II) complexhydrogen bond<i>cis/trans</i> isomerization |
| spellingShingle | Masumi Itazaki Kento Okabayashi Takanari Matsutani Tomoya Nochida Toshiyuki Moriuchi Hiroshi Nakazawa Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex Molecules hydrophosphination phosphinecarboxamide phosphinecarbothioamide palladium(II) complex hydrogen bond <i>cis/trans</i> isomerization |
| title | Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex |
| title_full | Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex |
| title_fullStr | Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex |
| title_full_unstemmed | Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex |
| title_short | Synthesis and Characterization of Phosphinecarboxamide and Phosphinecarbothioamide, and Their Complexation with Palladium(II) Complex |
| title_sort | synthesis and characterization of phosphinecarboxamide and phosphinecarbothioamide and their complexation with palladium ii complex |
| topic | hydrophosphination phosphinecarboxamide phosphinecarbothioamide palladium(II) complex hydrogen bond <i>cis/trans</i> isomerization |
| url | https://www.mdpi.com/1420-3049/27/17/5564 |
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