Platinum (IV) azido complexes undergo copper-free click reactions with alkynes
<p>We report our investigations into the first examples of copper-free 1,3-dipolar cycloaddition (click) reactions of electrophiles with a Pt<small><sup>IV</sup></small> azido complex. The Pt-<small><sup>IV</sup></small> azido complex <em>t...
| Main Authors: | , , , , |
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| Format: | Journal article |
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Royal Society of Chemistry
2018
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| _version_ | 1797106109685694464 |
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| author | Farrer, NJ Sharma, G Sayers, R Shaili, E Sadler, P |
| author_facet | Farrer, NJ Sharma, G Sayers, R Shaili, E Sadler, P |
| author_sort | Farrer, NJ |
| collection | OXFORD |
| description | <p>We report our investigations into the first examples of copper-free 1,3-dipolar cycloaddition (click) reactions of electrophiles with a Pt<small><sup>IV</sup></small> azido complex. The Pt-<small><sup>IV</sup></small> azido complex <em>trans</em>, <em>trans</em>, <em>trans</em>-[Pt<small><sup>IV</sup></small>(py)<small><sub>2</sub></small>(N<small><sub>3</sub></small>)<small><sub>2</sub></small>(OH)<small><sub>2</sub></small>] (<strong>1</strong>) was reactive towards dimethyl acetylenedicarboxylate (DMAD) (<strong>2</strong>), diethyl acetylenedicarboxylate DEACD (<strong>3</strong>), <em>N</em>-[(1<em>R</em>,8<em>S</em>,9<em>s</em>)-bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane (BCN) (<strong>11</strong>) and dibenzocyclooctyne-amine (DBCO) (<strong>12</strong>) resulting in formation of the corresponding mono (a) and bis-substituted (b) complexes. Complexes of <strong>2</strong> undergo further reactions between the Pt centre and the carbonyl group to form <strong>2a′</strong> and <strong>2b′</strong>. This is not seen for the products of the corresponding Pt<small><sup>II</sup></small> azido complex <em>trans</em>-[Pt(py)<small><sub>2</sub></small>(N<small><sub>3</sub></small>)<small><sub>2</sub></small>] with acetylene <strong>2</strong>. Novel complexes <strong>2a′</strong>, <strong>2b′</strong>, <strong>11a</strong> and <strong>11b</strong> have been characterised by multinuclear NMR, IR and UV-vis spectroscopy and ESI-MS. These reactions represent new synthetic routes to novel Pt(<small>IV</small>) complexes.</p> |
| first_indexed | 2024-03-07T06:57:03Z |
| format | Journal article |
| id | oxford-uuid:fe79b640-1099-4699-a13d-6b61120a8004 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T06:57:03Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:fe79b640-1099-4699-a13d-6b61120a80042022-03-27T13:36:53ZPlatinum (IV) azido complexes undergo copper-free click reactions with alkynesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fe79b640-1099-4699-a13d-6b61120a8004Symplectic Elements at OxfordRoyal Society of Chemistry2018Farrer, NJSharma, GSayers, RShaili, ESadler, P<p>We report our investigations into the first examples of copper-free 1,3-dipolar cycloaddition (click) reactions of electrophiles with a Pt<small><sup>IV</sup></small> azido complex. The Pt-<small><sup>IV</sup></small> azido complex <em>trans</em>, <em>trans</em>, <em>trans</em>-[Pt<small><sup>IV</sup></small>(py)<small><sub>2</sub></small>(N<small><sub>3</sub></small>)<small><sub>2</sub></small>(OH)<small><sub>2</sub></small>] (<strong>1</strong>) was reactive towards dimethyl acetylenedicarboxylate (DMAD) (<strong>2</strong>), diethyl acetylenedicarboxylate DEACD (<strong>3</strong>), <em>N</em>-[(1<em>R</em>,8<em>S</em>,9<em>s</em>)-bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane (BCN) (<strong>11</strong>) and dibenzocyclooctyne-amine (DBCO) (<strong>12</strong>) resulting in formation of the corresponding mono (a) and bis-substituted (b) complexes. Complexes of <strong>2</strong> undergo further reactions between the Pt centre and the carbonyl group to form <strong>2a′</strong> and <strong>2b′</strong>. This is not seen for the products of the corresponding Pt<small><sup>II</sup></small> azido complex <em>trans</em>-[Pt(py)<small><sub>2</sub></small>(N<small><sub>3</sub></small>)<small><sub>2</sub></small>] with acetylene <strong>2</strong>. Novel complexes <strong>2a′</strong>, <strong>2b′</strong>, <strong>11a</strong> and <strong>11b</strong> have been characterised by multinuclear NMR, IR and UV-vis spectroscopy and ESI-MS. These reactions represent new synthetic routes to novel Pt(<small>IV</small>) complexes.</p> |
| spellingShingle | Farrer, NJ Sharma, G Sayers, R Shaili, E Sadler, P Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title | Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title_full | Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title_fullStr | Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title_full_unstemmed | Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title_short | Platinum (IV) azido complexes undergo copper-free click reactions with alkynes |
| title_sort | platinum iv azido complexes undergo copper free click reactions with alkynes |
| work_keys_str_mv | AT farrernj platinumivazidocomplexesundergocopperfreeclickreactionswithalkynes AT sharmag platinumivazidocomplexesundergocopperfreeclickreactionswithalkynes AT sayersr platinumivazidocomplexesundergocopperfreeclickreactionswithalkynes AT shailie platinumivazidocomplexesundergocopperfreeclickreactionswithalkynes AT sadlerp platinumivazidocomplexesundergocopperfreeclickreactionswithalkynes |