Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes
Nickel-catalyzed 1,2-carboboration of alkenes is emerging as a useful method for chemical synthesis. Prior studies have been limited to only the incorporation of aryl groups. In this manuscript, a method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily av...
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| Veröffentlicht in: | Chemical science (Cambridge) 2019-12, Vol.1 (47), p.1944-1947 |
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| creator | Joung, Seewon Bergmann, Allison M Brown, M. Kevin |
| description | Nickel-catalyzed 1,2-carboboration of alkenes is emerging as a useful method for chemical synthesis. Prior studies have been limited to only the incorporation of aryl groups. In this manuscript, a method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry. The utility of the products as well as the mechanistic details of the process are also presented.
A method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry. |
| doi_str_mv | 10.1039/c9sc04199k |
| format | Article |
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A method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c9sc04199k</identifier><identifier>PMID: 32190251</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Aromatic compounds ; Chemical synthesis ; Chemistry ; Nickel ; Organic chemistry ; Reagents ; Stereochemistry</subject><ispartof>Chemical science (Cambridge), 2019-12, Vol.1 (47), p.1944-1947</ispartof><rights>This journal is © The Royal Society of Chemistry 2019.</rights><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c520t-f495ea9b8f9676446172295b1d814e24ad1fedee65b445612eee97f84b8b0e503</citedby><cites>FETCH-LOGICAL-c520t-f495ea9b8f9676446172295b1d814e24ad1fedee65b445612eee97f84b8b0e503</cites><orcidid>0000-0002-4993-0917 ; 0000-0002-6989-444X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066668/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066668/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,861,882,27905,27906,53772,53774</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32190251$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Joung, Seewon</creatorcontrib><creatorcontrib>Bergmann, Allison M</creatorcontrib><creatorcontrib>Brown, M. Kevin</creatorcontrib><title>Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>Nickel-catalyzed 1,2-carboboration of alkenes is emerging as a useful method for chemical synthesis. Prior studies have been limited to only the incorporation of aryl groups. In this manuscript, a method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry. The utility of the products as well as the mechanistic details of the process are also presented.
A method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry.</description><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Reagents</subject><subject>Stereochemistry</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kcsvBTEYxRshyGVjT4iNiKGveXQjkRuvEBZYN23nG8rc6dV2JNdfr1yux8K36ZeeX05OexBaI3ifYCYOjAgGcyLE0xxapmnLipyJ-dlO8RJaDeERp2GM5LRcREuMEoFpTpbR2ZXNjIqqnbxCvUn2aKahe5202nkVres2XfNxW9vQ6xBt7GPi-k6ZaF_U-67aJ-ggrKCFRrUBVj_PAbo7Ob4dnmWX16fnw6PLzKQoMWu4yEEJXTWiKAvOC1JSKnJN6opwoFzVpIEaoMg153lBKACIsqm4rjSGHLMBOpz6jns9gtpAF71q5djbkfIT6ZSVv5XOPsh79yJLXKSpksHOp4F3zz2EKEc2GGhb1YHrg6SsTH-DOSsTuv0HfXS979LzEkWxoLTiIlG7U8p4F4KHZhaGYPnekRyKm-FHRxcJ3vgZf4Z-NZKA9Sngg5mp3yUnfes_XY7rhr0BU9Gg-Q</recordid><startdate>20191221</startdate><enddate>20191221</enddate><creator>Joung, Seewon</creator><creator>Bergmann, Allison M</creator><creator>Brown, M. Kevin</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4993-0917</orcidid><orcidid>https://orcid.org/0000-0002-6989-444X</orcidid></search><sort><creationdate>20191221</creationdate><title>Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes</title><author>Joung, Seewon ; Bergmann, Allison M ; Brown, M. Kevin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c520t-f495ea9b8f9676446172295b1d814e24ad1fedee65b445612eee97f84b8b0e503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Reagents</topic><topic>Stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Joung, Seewon</creatorcontrib><creatorcontrib>Bergmann, Allison M</creatorcontrib><creatorcontrib>Brown, M. Kevin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Joung, Seewon</au><au>Bergmann, Allison M</au><au>Brown, M. Kevin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2019-12-21</date><risdate>2019</risdate><volume>1</volume><issue>47</issue><spage>1944</spage><epage>1947</epage><pages>1944-1947</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Nickel-catalyzed 1,2-carboboration of alkenes is emerging as a useful method for chemical synthesis. Prior studies have been limited to only the incorporation of aryl groups. In this manuscript, a method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry. The utility of the products as well as the mechanistic details of the process are also presented.
A method for the 1,2-benzylboration of unactivated alkenes is presented. The reaction combines readily available alkenes, diboron reagents and benzylchlorides to generate synthetically versatile products with control of stereochemistry.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32190251</pmid><doi>10.1039/c9sc04199k</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4993-0917</orcidid><orcidid>https://orcid.org/0000-0002-6989-444X</orcidid><oa>free_for_read</oa></addata></record> |
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| source | PMC (PubMed Central); DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals |
| subjects | Alkenes Aromatic compounds Chemical synthesis Chemistry Nickel Organic chemistry Reagents Stereochemistry |
| title | Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes |
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