Functionalization of closo-Borates via Iodonium Zwitterions
A simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)2]− (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-05, Vol.54 (22), p.6576-6581 |
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| creator | Kaszyński, Piotr Ringstrand, Bryan |
| description | A simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)2]− (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were sufficiently stable for chromatographic purification. The reactions of these zwitterions with nucleophiles provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino derivatives. The synthetic results are augmented by mechanistic considerations.
Openo to change: The simple preparation of iodonium zwitterions of closo‐borates and their reactions with nucleophiles (see scheme) provided access to a broad spectrum of cluster derivatives with potential as new classes of pharmaceuticals and materials with tailored properties. The presented reactions demonstrate the synthetic versatility of closo‐borate aryliodonium zwitterions. |
| doi_str_mv | 10.1002/anie.201411858 |
| format | Article |
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Openo to change: The simple preparation of iodonium zwitterions of closo‐borates and their reactions with nucleophiles (see scheme) provided access to a broad spectrum of cluster derivatives with potential as new classes of pharmaceuticals and materials with tailored properties. The presented reactions demonstrate the synthetic versatility of closo‐borate aryliodonium zwitterions.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201411858</identifier><identifier>PMID: 25877873</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Borates - chemistry ; closo-borates ; cluster compounds ; functionalization ; Iodides - chemistry ; iodonium zwitterions ; Ions - chemistry ; Pyridines - chemistry ; Stereoisomerism ; Sulfhydryl Compounds - chemistry ; Sulfones - chemistry ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2015-05, Vol.54 (22), p.6576-6581</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5848-6b484122ec3df463a39b23fbc639142aa2076da6c4fea2fc92356a8bbed538ce3</citedby><cites>FETCH-LOGICAL-c5848-6b484122ec3df463a39b23fbc639142aa2076da6c4fea2fc92356a8bbed538ce3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201411858$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201411858$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25877873$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaszyński, Piotr</creatorcontrib><creatorcontrib>Ringstrand, Bryan</creatorcontrib><title>Functionalization of closo-Borates via Iodonium Zwitterions</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)2]− (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were sufficiently stable for chromatographic purification. The reactions of these zwitterions with nucleophiles provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino derivatives. The synthetic results are augmented by mechanistic considerations.
Openo to change: The simple preparation of iodonium zwitterions of closo‐borates and their reactions with nucleophiles (see scheme) provided access to a broad spectrum of cluster derivatives with potential as new classes of pharmaceuticals and materials with tailored properties. The presented reactions demonstrate the synthetic versatility of closo‐borate aryliodonium zwitterions.</description><subject>Borates - chemistry</subject><subject>closo-borates</subject><subject>cluster compounds</subject><subject>functionalization</subject><subject>Iodides - chemistry</subject><subject>iodonium zwitterions</subject><subject>Ions - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Stereoisomerism</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfones - chemistry</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDtPwzAUhS0E4r0yokgsLCmxr2O7YoIKSikqAyAkFstxHMmQxmAnvH49rgIVYmG6Z_jOJ92D0B7OBjjLyJFqrBmQDFOMRS5W0CbOCU6Bc1iNmQKkXOR4A22F8Bh5ITK2jjZILjgXHDbR8XnX6Na6RtX2Uy1C4qpE1y649NR51ZqQvFqVTFzpGtvNk4c327bGRzDsoLVK1cHsft9tdHd-dju6SK-ux5PRyVWqc0FFygoqKCbEaCgrykDBsCBQFZrBEFOiFMk4KxXTtDKKVHpIIGdKFIUpcxDawDY67L3P3r10JrRyboM2da0a47ogMRPA8yjDET34gz66zsfnegoDo4RGatBT2rsQvKnks7dz5T8kzuRiVrmYVS5njYX9b21XzE25xH92jMCwB95sbT7-0cmT2eTstzztuza05n3ZVf5JMh4fk_ezsbyZwnR6OWLyFr4A09mStg</recordid><startdate>20150526</startdate><enddate>20150526</enddate><creator>Kaszyński, Piotr</creator><creator>Ringstrand, Bryan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150526</creationdate><title>Functionalization of closo-Borates via Iodonium Zwitterions</title><author>Kaszyński, Piotr ; Ringstrand, Bryan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5848-6b484122ec3df463a39b23fbc639142aa2076da6c4fea2fc92356a8bbed538ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Borates - chemistry</topic><topic>closo-borates</topic><topic>cluster compounds</topic><topic>functionalization</topic><topic>Iodides - chemistry</topic><topic>iodonium zwitterions</topic><topic>Ions - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Stereoisomerism</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfones - chemistry</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaszyński, Piotr</creatorcontrib><creatorcontrib>Ringstrand, Bryan</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaszyński, Piotr</au><au>Ringstrand, Bryan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Functionalization of closo-Borates via Iodonium Zwitterions</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-05-26</date><risdate>2015</risdate><volume>54</volume><issue>22</issue><spage>6576</spage><epage>6581</epage><pages>6576-6581</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)2]− (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were sufficiently stable for chromatographic purification. The reactions of these zwitterions with nucleophiles provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino derivatives. The synthetic results are augmented by mechanistic considerations.
Openo to change: The simple preparation of iodonium zwitterions of closo‐borates and their reactions with nucleophiles (see scheme) provided access to a broad spectrum of cluster derivatives with potential as new classes of pharmaceuticals and materials with tailored properties. The presented reactions demonstrate the synthetic versatility of closo‐borate aryliodonium zwitterions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25877873</pmid><doi>10.1002/anie.201411858</doi><tpages>6</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Borates - chemistry closo-borates cluster compounds functionalization Iodides - chemistry iodonium zwitterions Ions - chemistry Pyridines - chemistry Stereoisomerism Sulfhydryl Compounds - chemistry Sulfones - chemistry synthetic methods |
| title | Functionalization of closo-Borates via Iodonium Zwitterions |
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