Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration
A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reac...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (6), p.1024-1026 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Li, Yang Liu, Bang Li, Hai-Bing Wang, Qiuan Li, Jin-Heng |
| description | A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation. |
| doi_str_mv | 10.1039/c4cc08902b |
| format | Article |
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In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c4cc08902b</identifier><identifier>PMID: 25446150</identifier><language>eng</language><publisher>England</publisher><subject>Acetonitrile ; Alkenes ; Carbon-carbon composites ; Chemical bonds ; Coupling (molecular) ; Migration ; Radicals ; Synthesis</subject><ispartof>Chemical communications (Cambridge, England), 2015-01, Vol.51 (6), p.1024-1026</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c320t-8aee5720fad5f0ef9a6e633dbd5146e62d3e544e0805f4fd78131087303f84333</citedby><cites>FETCH-LOGICAL-c320t-8aee5720fad5f0ef9a6e633dbd5146e62d3e544e0805f4fd78131087303f84333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25446150$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Liu, Bang</creatorcontrib><creatorcontrib>Li, Hai-Bing</creatorcontrib><creatorcontrib>Wang, Qiuan</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><title>Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.</description><subject>Acetonitrile</subject><subject>Alkenes</subject><subject>Carbon-carbon composites</subject><subject>Chemical bonds</subject><subject>Coupling (molecular)</subject><subject>Migration</subject><subject>Radicals</subject><subject>Synthesis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkc9KAzEQh4MotlYvPoDssRVXk51kNznqolYo9KLgbclukhrdP3WzXfWxfBGfybRVrw4MMwwfHww_hI4JPicYxEVBiwJzgaN8Bw0JxDRklD_urncmwgQoG6AD556xL8L4PhpEjNKYMDxE_fzdKtnZXgetVLaQZUDOolCWLx-lbH13tqmDxgT-omvtgjfbPQVfn2E6dssxTCbhNMibWrkNU-iuqW3X2tKTtu6bsrf1Ymv0sqCyi3ZjPER7RpZOH_3MEXq4ub5Pp-FsfnuXXs7CAiLchVxqzZIIG6mYwdoIGesYQOWKEerXSIH2r2jMMTPUqIQTIJgngMFwCgAjNN56l23zutKuyyrrCl2WstbNymWEC-CCJZz9j8YgqABga_R0ixZt41yrTbZsbeU_zAjO1pFkKU3TTSRXHj758a7ySqs_9DcD-AY1zoXf</recordid><startdate>20150121</startdate><enddate>20150121</enddate><creator>Li, Yang</creator><creator>Liu, Bang</creator><creator>Li, Hai-Bing</creator><creator>Wang, Qiuan</creator><creator>Li, Jin-Heng</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150121</creationdate><title>Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration</title><author>Li, Yang ; Liu, Bang ; Li, Hai-Bing ; Wang, Qiuan ; Li, Jin-Heng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-8aee5720fad5f0ef9a6e633dbd5146e62d3e544e0805f4fd78131087303f84333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetonitrile</topic><topic>Alkenes</topic><topic>Carbon-carbon composites</topic><topic>Chemical bonds</topic><topic>Coupling (molecular)</topic><topic>Migration</topic><topic>Radicals</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Liu, Bang</creatorcontrib><creatorcontrib>Li, Hai-Bing</creatorcontrib><creatorcontrib>Wang, Qiuan</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</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><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Yang</au><au>Liu, Bang</au><au>Li, Hai-Bing</au><au>Wang, Qiuan</au><au>Li, Jin-Heng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2015-01-21</date><risdate>2015</risdate><volume>51</volume><issue>6</issue><spage>1024</spage><epage>1026</epage><pages>1024-1026</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.</abstract><cop>England</cop><pmid>25446150</pmid><doi>10.1039/c4cc08902b</doi><tpages>3</tpages></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2015-01, Vol.51 (6), p.1024-1026 |
| issn | 1359-7345 1364-548X |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetonitrile Alkenes Carbon-carbon composites Chemical bonds Coupling (molecular) Migration Radicals Synthesis |
| title | Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration |
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