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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chinese journal of chemistry 2019-08, Vol.37 (8), p.781-785
Hauptverfasser: Cao, Zhi‐Chao, Xu, Pei‐Lin, Luo, Qin‐Yu, Li, Xiao‐Lei, Yu, Da‐Gang, Fang, Huayi, Shi, Zhang‐Jie
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 785
container_issue 8
container_start_page 781
container_title Chinese journal of chemistry
container_volume 37
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
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2288860377</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2288860377</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3544-9b9e044f228711a0e19262395ea51efeac41c1bf28a0526958e5739ea9cce78a3</originalsourceid><addsrcrecordid>eNqFkEFLAzEQRoMoWKtXzwHPWyfZZLM5ylq1UuhFwVtI01nYsk1qsq3035tS0aOnmYH3fQOPkFsGEwbA7906uAkHVgNIKc7IiFVMFAoqeZ53AFZUID4uyVVK68wrxasReWyC32NMXfA0tLSxcRn8oadN2GzDzq8SHQJd9Nh2PtF9Z-nUh94OSGd-wLjBVZePa3LR2j7hzc8ck_en6VvzUswXz7PmYV64UgpR6KVGEKLlvFaMWUCmecVLLdFKhi1aJ5hjy5bXFiSvtKxRqlKj1c6hqm05Jnen3m0MnztMg1mHXfT5pcmddV1BqVSmJifKxZBSxNZsY7ex8WAYmKMpczRlfk3lgD4FvroeD__QpnldNH_ZbxqYbE0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2288860377</pqid></control><display><type>article</type><title>Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate</title><source>Wiley Online Library All Journals</source><creator>Cao, Zhi‐Chao ; Xu, Pei‐Lin ; Luo, Qin‐Yu ; Li, Xiao‐Lei ; Yu, Da‐Gang ; Fang, Huayi ; Shi, Zhang‐Jie</creator><creatorcontrib>Cao, Zhi‐Chao ; Xu, Pei‐Lin ; Luo, Qin‐Yu ; Li, Xiao‐Lei ; Yu, Da‐Gang ; Fang, Huayi ; Shi, Zhang‐Jie</creatorcontrib><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><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 &amp; 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, &amp; WILEY‐VCH Verlag GmbH &amp; 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 &amp; 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 &amp; Co. KGaA</pub><doi>10.1002/cjoc.201800554</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1001-604X
ispartof Chinese journal of chemistry, 2019-08, Vol.37 (8), p.781-785
issn 1001-604X
1614-7065
language eng
recordid cdi_proquest_journals_2288860377
source Wiley Online Library All Journals
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
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T23%3A36%3A54IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Conversion%20of%20Carbonyl%20Compounds%20to%20Olefins%20via%20Enolate%20Intermediate&rft.jtitle=Chinese%20journal%20of%20chemistry&rft.au=Cao,%20Zhi%E2%80%90Chao&rft.date=2019-08&rft.volume=37&rft.issue=8&rft.spage=781&rft.epage=785&rft.pages=781-785&rft.issn=1001-604X&rft.eissn=1614-7065&rft_id=info:doi/10.1002/cjoc.201800554&rft_dat=%3Cproquest_cross%3E2288860377%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2288860377&rft_id=info:pmid/&rfr_iscdi=true