Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf]
The structure of Stang's reagent [PhI(CN)][OTf] is confirmed by X-ray crystallography and is determined to be best described as an ion-pair in organic solution. It is found to be a strong Lewis acid, but reaction with pyridine ligands gives [Pyr-CN][OTf] salts via oxidation of pyridine giving a...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2023-06, Vol.52 (25), p.8536-8539 |
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| container_end_page | 8539 |
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| container_issue | 25 |
| container_start_page | 8536 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 52 |
| creator | Bennetts, Jason D Barwise, Lachlan Sharp-Bucknall, Lachlan White, Keith F Hogan, Conor F Dutton, Jason L |
| description | The structure of Stang's reagent [PhI(CN)][OTf] is confirmed by X-ray crystallography and is determined to be best described as an ion-pair in organic solution. It is found to be a strong Lewis acid, but reaction with pyridine ligands gives [Pyr-CN][OTf] salts
via
oxidation of pyridine giving a new derivative of the CDAP reagent widely used as an activation agent for polysaccharides.
The solid-state structure of Stang's reagent is revealed, with confirmation of its existence as an ion-pair with triflate in solution. Further reactivity successfully delivers CN to pyridyl ligands. |
| doi_str_mv | 10.1039/d3dt01765f |
| format | Article |
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via
oxidation of pyridine giving a new derivative of the CDAP reagent widely used as an activation agent for polysaccharides.
The solid-state structure of Stang's reagent is revealed, with confirmation of its existence as an ion-pair with triflate in solution. Further reactivity successfully delivers CN to pyridyl ligands.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d3dt01765f</identifier><identifier>PMID: 37325880</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Crystallography ; Ion pairs ; Lewis acid ; Oxidation ; Polysaccharides ; Pyridines ; Reagents</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2023-06, Vol.52 (25), p.8536-8539</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c296t-f496f45e4bafe23fc3eb61436d84636d9de4b8cd41038b019d8760b9ef78520a3</cites><orcidid>0000-0002-0361-4441 ; 0000-0001-8250-3098 ; 0000-0003-2800-1104</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37325880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bennetts, Jason D</creatorcontrib><creatorcontrib>Barwise, Lachlan</creatorcontrib><creatorcontrib>Sharp-Bucknall, Lachlan</creatorcontrib><creatorcontrib>White, Keith F</creatorcontrib><creatorcontrib>Hogan, Conor F</creatorcontrib><creatorcontrib>Dutton, Jason L</creatorcontrib><title>Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf]</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>The structure of Stang's reagent [PhI(CN)][OTf] is confirmed by X-ray crystallography and is determined to be best described as an ion-pair in organic solution. It is found to be a strong Lewis acid, but reaction with pyridine ligands gives [Pyr-CN][OTf] salts
via
oxidation of pyridine giving a new derivative of the CDAP reagent widely used as an activation agent for polysaccharides.
The solid-state structure of Stang's reagent is revealed, with confirmation of its existence as an ion-pair with triflate in solution. Further reactivity successfully delivers CN to pyridyl ligands.</description><subject>Crystallography</subject><subject>Ion pairs</subject><subject>Lewis acid</subject><subject>Oxidation</subject><subject>Polysaccharides</subject><subject>Pyridines</subject><subject>Reagents</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0UFPwjAUB_DGaATRi3fNEg-icdq1XdceDYiaEDABT4QsXdfiCGzYdhi-vZsgJl7apu-Xl9d_ATgP4H0AMX9IcepgENFQH4BmQKLI5wiTw_0Z0QY4sXYOIUIwRMeggSOMQsZgEwxGzpTSlUYsvLUymc6kcFmReyJPvVx9eUYJ6bJ15jaeLow3ciKfXdv6eqZyd-dN3j5e253BzXQyHOvpKTjSYmHV2W5vgffe07jz4veHz6-dx74vEafO14RTTUJFEqEVwlpildCAYJoyQquVp1WJyZRU72MJDHjKIgoTrnTEQgQFboH2tu_KFJ-lsi5eZlaqxULkqihtjBiKEEU0hBW9-kfnRWnyarpacRoiRmp1u1XSFNYapeOVyZbCbOIAxnXKcRd3xz8p9yp8uWtZJkuV7ulvrBW42AJj5b769034G4kUf48</recordid><startdate>20230627</startdate><enddate>20230627</enddate><creator>Bennetts, Jason D</creator><creator>Barwise, Lachlan</creator><creator>Sharp-Bucknall, Lachlan</creator><creator>White, Keith F</creator><creator>Hogan, Conor F</creator><creator>Dutton, Jason L</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0361-4441</orcidid><orcidid>https://orcid.org/0000-0001-8250-3098</orcidid><orcidid>https://orcid.org/0000-0003-2800-1104</orcidid></search><sort><creationdate>20230627</creationdate><title>Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf]</title><author>Bennetts, Jason D ; Barwise, Lachlan ; Sharp-Bucknall, Lachlan ; White, Keith F ; Hogan, Conor F ; Dutton, Jason L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-f496f45e4bafe23fc3eb61436d84636d9de4b8cd41038b019d8760b9ef78520a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Crystallography</topic><topic>Ion pairs</topic><topic>Lewis acid</topic><topic>Oxidation</topic><topic>Polysaccharides</topic><topic>Pyridines</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bennetts, Jason D</creatorcontrib><creatorcontrib>Barwise, Lachlan</creatorcontrib><creatorcontrib>Sharp-Bucknall, Lachlan</creatorcontrib><creatorcontrib>White, Keith F</creatorcontrib><creatorcontrib>Hogan, Conor F</creatorcontrib><creatorcontrib>Dutton, Jason L</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bennetts, Jason D</au><au>Barwise, Lachlan</au><au>Sharp-Bucknall, Lachlan</au><au>White, Keith F</au><au>Hogan, Conor F</au><au>Dutton, Jason L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf]</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2023-06-27</date><risdate>2023</risdate><volume>52</volume><issue>25</issue><spage>8536</spage><epage>8539</epage><pages>8536-8539</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>The structure of Stang's reagent [PhI(CN)][OTf] is confirmed by X-ray crystallography and is determined to be best described as an ion-pair in organic solution. It is found to be a strong Lewis acid, but reaction with pyridine ligands gives [Pyr-CN][OTf] salts
via
oxidation of pyridine giving a new derivative of the CDAP reagent widely used as an activation agent for polysaccharides.
The solid-state structure of Stang's reagent is revealed, with confirmation of its existence as an ion-pair with triflate in solution. Further reactivity successfully delivers CN to pyridyl ligands.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37325880</pmid><doi>10.1039/d3dt01765f</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0361-4441</orcidid><orcidid>https://orcid.org/0000-0001-8250-3098</orcidid><orcidid>https://orcid.org/0000-0003-2800-1104</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2023-06, Vol.52 (25), p.8536-8539 |
| issn | 1477-9226 1477-9234 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Crystallography Ion pairs Lewis acid Oxidation Polysaccharides Pyridines Reagents |
| title | Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf] |
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