An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction
A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. En...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2016-01, Vol.11 (2), p.193-197 |
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| container_end_page | 197 |
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| container_issue | 2 |
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| container_title | Chemistry, an Asian journal |
| container_volume | 11 |
| creator | Han, Runfeng He, Liwenze Liu, Lin Xie, Xingang She, Xuegong |
| description | A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. Enantiomeric excess of the major product in the cycloaddition reaction remained intact in the follow‐up sulfonyl migration reaction.
Valuable by‐product: A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. The enantiomeric excess of the major product in the cycloaddition reaction was retained in the follow‐up sulfonyl migration reaction. |
| doi_str_mv | 10.1002/asia.201500959 |
| format | Article |
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Valuable by‐product: A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. The enantiomeric excess of the major product in the cycloaddition reaction was retained in the follow‐up sulfonyl migration reaction.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201500959</identifier><identifier>PMID: 26522328</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Catalysis ; Chemistry ; ester activation ; N-heterocyclic carbenes ; N-hydroxyphthalimide ; radicals ; sulfonyl migration</subject><ispartof>Chemistry, an Asian journal, 2016-01, Vol.11 (2), p.193-197</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4489-19afd82e86a93774eb3716146e35ef9f336b1b39b675929f91868bf1e74825c53</citedby><cites>FETCH-LOGICAL-c4489-19afd82e86a93774eb3716146e35ef9f336b1b39b675929f91868bf1e74825c53</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%2Fasia.201500959$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201500959$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26522328$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Runfeng</creatorcontrib><creatorcontrib>He, Liwenze</creatorcontrib><creatorcontrib>Liu, Lin</creatorcontrib><creatorcontrib>Xie, Xingang</creatorcontrib><creatorcontrib>She, Xuegong</creatorcontrib><title>An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. Enantiomeric excess of the major product in the cycloaddition reaction remained intact in the follow‐up sulfonyl migration reaction.
Valuable by‐product: A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. The enantiomeric excess of the major product in the cycloaddition reaction was retained in the follow‐up sulfonyl migration reaction.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>ester activation</subject><subject>N-heterocyclic carbenes</subject><subject>N-hydroxyphthalimide</subject><subject>radicals</subject><subject>sulfonyl migration</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAUhSMEoqWwZYkssWGTqa8dv5bp0JdUCupD7c5yMjZyyWOwk5bw6-tRhhFiw-qexXeO7r0ny94DXgDG5NBEbxYEA8NYMfUi2wfJIS8E3L_caSL3sjcxPmDMCFbydbZHOCOEErmf9WWHbtdxCNa06GjK16FfjfWAXOhbdBwHG1BZD_7RDL7v0KM36PJsmS_NYJop-ohm9dtG9Ll_6rY512Pj-m5q0Bf_PczOK2vqjXibvXKmifbddh5ktyfHN8uz_OLr6fmyvMjropAqB2XcShIruVFUiMJWVACHglvKrFOOUl5BRVXFBVNEOZVOlZUDKwpJWM3oQfZpzk0H_RxtHHTrY22bxnS2H6MGwQFLACkS-vEf9KEfQ5e221DprxRAJWoxU3XoYwzW6XXwrQmTBqw3VehNFXpXRTJ82MaOVWtXO_zP7xOgZuDJN3b6T5wur8_Lv8Pz2etTRb92XhN-aC6oYPru8lRfndx9g5uje03pM-XspCM</recordid><startdate>201601</startdate><enddate>201601</enddate><creator>Han, Runfeng</creator><creator>He, Liwenze</creator><creator>Liu, Lin</creator><creator>Xie, Xingang</creator><creator>She, Xuegong</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>201601</creationdate><title>An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction</title><author>Han, Runfeng ; He, Liwenze ; Liu, Lin ; Xie, Xingang ; She, Xuegong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4489-19afd82e86a93774eb3716146e35ef9f336b1b39b675929f91868bf1e74825c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>ester activation</topic><topic>N-heterocyclic carbenes</topic><topic>N-hydroxyphthalimide</topic><topic>radicals</topic><topic>sulfonyl migration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Runfeng</creatorcontrib><creatorcontrib>He, Liwenze</creatorcontrib><creatorcontrib>Liu, Lin</creatorcontrib><creatorcontrib>Xie, Xingang</creatorcontrib><creatorcontrib>She, Xuegong</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Runfeng</au><au>He, Liwenze</au><au>Liu, Lin</au><au>Xie, Xingang</au><au>She, Xuegong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2016-01</date><risdate>2016</risdate><volume>11</volume><issue>2</issue><spage>193</spage><epage>197</epage><pages>193-197</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. Enantiomeric excess of the major product in the cycloaddition reaction remained intact in the follow‐up sulfonyl migration reaction.
Valuable by‐product: A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. The enantiomeric excess of the major product in the cycloaddition reaction was retained in the follow‐up sulfonyl migration reaction.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26522328</pmid><doi>10.1002/asia.201500959</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 1861-4728 |
| ispartof | Chemistry, an Asian journal, 2016-01, Vol.11 (2), p.193-197 |
| issn | 1861-4728 1861-471X |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Catalysis Chemistry ester activation N-heterocyclic carbenes N-hydroxyphthalimide radicals sulfonyl migration |
| title | An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction |
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