Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate
Summary of main observation and conclusion A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce...
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Veröffentlicht in: | Chinese journal of chemistry 2019-08, Vol.37 (8), p.781-785 |
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container_title | Chinese journal of chemistry |
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creator | Cao, Zhi‐Chao Xu, Pei‐Lin Luo, Qin‐Yu Li, Xiao‐Lei Yu, Da‐Gang Fang, Huayi Shi, Zhang‐Jie |
description | Summary of main observation and conclusion
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di‐ or tri‐ substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio‐ and stereo‐selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry. |
doi_str_mv | 10.1002/cjoc.201800554 |
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A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di‐ or tri‐ substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio‐ and stereo‐selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.201800554</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Activation ; Alcohols ; Aldehydes ; Alkenes ; Carbonyl compounds ; Carbonyls ; Catalysis ; Ketones ; Nickel ; Organic chemistry ; Selectivity ; Substitutes ; Substrates</subject><ispartof>Chinese journal of chemistry, 2019-08, Vol.37 (8), p.781-785</ispartof><rights>2019 SIOC, CAS, Shanghai, & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3544-9b9e044f228711a0e19262395ea51efeac41c1bf28a0526958e5739ea9cce78a3</citedby><cites>FETCH-LOGICAL-c3544-9b9e044f228711a0e19262395ea51efeac41c1bf28a0526958e5739ea9cce78a3</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%2Fcjoc.201800554$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.201800554$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Cao, Zhi‐Chao</creatorcontrib><creatorcontrib>Xu, Pei‐Lin</creatorcontrib><creatorcontrib>Luo, Qin‐Yu</creatorcontrib><creatorcontrib>Li, Xiao‐Lei</creatorcontrib><creatorcontrib>Yu, Da‐Gang</creatorcontrib><creatorcontrib>Fang, Huayi</creatorcontrib><creatorcontrib>Shi, Zhang‐Jie</creatorcontrib><title>Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate</title><title>Chinese journal of chemistry</title><description>Summary of main observation and conclusion
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di‐ or tri‐ substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio‐ and stereo‐selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.</description><subject>Activation</subject><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Alkenes</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Catalysis</subject><subject>Ketones</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Selectivity</subject><subject>Substitutes</subject><subject>Substrates</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkEFLAzEQRoMoWKtXzwHPWyfZZLM5ylq1UuhFwVtI01nYsk1qsq3035tS0aOnmYH3fQOPkFsGEwbA7906uAkHVgNIKc7IiFVMFAoqeZ53AFZUID4uyVVK68wrxasReWyC32NMXfA0tLSxcRn8oadN2GzDzq8SHQJd9Nh2PtF9Z-nUh94OSGd-wLjBVZePa3LR2j7hzc8ck_en6VvzUswXz7PmYV64UgpR6KVGEKLlvFaMWUCmecVLLdFKhi1aJ5hjy5bXFiSvtKxRqlKj1c6hqm05Jnen3m0MnztMg1mHXfT5pcmddV1BqVSmJifKxZBSxNZsY7ex8WAYmKMpczRlfk3lgD4FvroeD__QpnldNH_ZbxqYbE0</recordid><startdate>201908</startdate><enddate>201908</enddate><creator>Cao, Zhi‐Chao</creator><creator>Xu, Pei‐Lin</creator><creator>Luo, Qin‐Yu</creator><creator>Li, Xiao‐Lei</creator><creator>Yu, Da‐Gang</creator><creator>Fang, Huayi</creator><creator>Shi, Zhang‐Jie</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201908</creationdate><title>Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate</title><author>Cao, Zhi‐Chao ; Xu, Pei‐Lin ; Luo, Qin‐Yu ; Li, Xiao‐Lei ; Yu, Da‐Gang ; Fang, Huayi ; Shi, Zhang‐Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3544-9b9e044f228711a0e19262395ea51efeac41c1bf28a0526958e5739ea9cce78a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Activation</topic><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Alkenes</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Catalysis</topic><topic>Ketones</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Selectivity</topic><topic>Substitutes</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cao, Zhi‐Chao</creatorcontrib><creatorcontrib>Xu, Pei‐Lin</creatorcontrib><creatorcontrib>Luo, Qin‐Yu</creatorcontrib><creatorcontrib>Li, Xiao‐Lei</creatorcontrib><creatorcontrib>Yu, Da‐Gang</creatorcontrib><creatorcontrib>Fang, Huayi</creatorcontrib><creatorcontrib>Shi, Zhang‐Jie</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cao, Zhi‐Chao</au><au>Xu, Pei‐Lin</au><au>Luo, Qin‐Yu</au><au>Li, Xiao‐Lei</au><au>Yu, Da‐Gang</au><au>Fang, Huayi</au><au>Shi, Zhang‐Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2019-08</date><risdate>2019</risdate><volume>37</volume><issue>8</issue><spage>781</spage><epage>785</epage><pages>781-785</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Summary of main observation and conclusion
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di‐ or tri‐ substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio‐ and stereo‐selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.201800554</doi><tpages>5</tpages></addata></record> |
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subjects | Activation Alcohols Aldehydes Alkenes Carbonyl compounds Carbonyls Catalysis Ketones Nickel Organic chemistry Selectivity Substitutes Substrates |
title | Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate |
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