Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis
The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Prelimi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-01, Vol.54 (4), p.1261-1265 |
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| creator | Liu, Jianming Zhang, Xin Yi, Hong Liu, Chao Liu, Ren Zhang, Heng Zhuo, Kelei Lei, Aiwen |
| description | The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N‐heterocyclic compounds and ethyl chloroacetate work synergistically to activate CH bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields.
Molecular oxygen can be used for the selective oxidation of CH bonds of N‐heterocyclic compounds to the corresponding ketones with a copper catalyst and ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. |
| doi_str_mv | 10.1002/anie.201409580 |
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Molecular oxygen can be used for the selective oxidation of CH bonds of N‐heterocyclic compounds to the corresponding ketones with a copper catalyst and ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201409580</identifier><identifier>PMID: 25483218</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Catalysts ; Copper ; copper catalysis ; ethyl chloroacetate ; Free radicals ; Ketones ; Methylene ; N-heterocycles ; Oxidation ; Radicals ; selective oxidations ; Transformations</subject><ispartof>Angewandte Chemie International Edition, 2015-01, Vol.54 (4), p.1261-1265</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6170-4594a3b8960f775890c17e9427b9ab0814e1778ec3399e2fe8682342759b24ea3</citedby><cites>FETCH-LOGICAL-c6170-4594a3b8960f775890c17e9427b9ab0814e1778ec3399e2fe8682342759b24ea3</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%2Fanie.201409580$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201409580$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27926,27927,45576,45577</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25483218$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Jianming</creatorcontrib><creatorcontrib>Zhang, Xin</creatorcontrib><creatorcontrib>Yi, Hong</creatorcontrib><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Liu, Ren</creatorcontrib><creatorcontrib>Zhang, Heng</creatorcontrib><creatorcontrib>Zhuo, Kelei</creatorcontrib><creatorcontrib>Lei, Aiwen</creatorcontrib><title>Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N‐heterocyclic compounds and ethyl chloroacetate work synergistically to activate CH bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields.
Molecular oxygen can be used for the selective oxidation of CH bonds of N‐heterocyclic compounds to the corresponding ketones with a copper catalyst and ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process.</description><subject>Catalysts</subject><subject>Copper</subject><subject>copper catalysis</subject><subject>ethyl chloroacetate</subject><subject>Free radicals</subject><subject>Ketones</subject><subject>Methylene</subject><subject>N-heterocycles</subject><subject>Oxidation</subject><subject>Radicals</subject><subject>selective oxidations</subject><subject>Transformations</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkUtP3DAURq2qqDzKlmUVqRs2mfoRx_YSRRSQKKC-2GE5mRth6omntgOkv74eDYwQG1bXks93_PgQOiB4RjCmX8xgYUYxqbDiEr9DO4RTUjIh2Pu8rhgrheRkG-3GeJd5KXH9AW1TXklGidxBN82t88GbDpJJUF4Fv_AJ5sUPcNAlew_F5aOdm2T9UPi-OIUEwbcw_Juc7YpvkG4nBwPEYhzmEIrGL5erYZJxU7TxI9rqjYuw_zT30K-vxz-b0_L88uSsOTovu5oIXFZcVYa1UtW4F4JLhTsiQFVUtMq0WJIKiBASOsaUAtqDrCVleZurllZg2B46XHuXwf8dISa9sLED58wAfow6H0IwxYyzt9GaUya5wiKjn1-hd34MQ35IpvKd81erlXC2prrgYwzQ62WwCxMmTbBelaRXJelNSTnw6Uk7tguYb_DnVjKg1sCDdTC9odNHF2fHL-XlOmtjgsdN1oQ_uhZMcH19caJ_E_Vd1VdYN-w_fbSrmg</recordid><startdate>20150119</startdate><enddate>20150119</enddate><creator>Liu, Jianming</creator><creator>Zhang, Xin</creator><creator>Yi, Hong</creator><creator>Liu, Chao</creator><creator>Liu, Ren</creator><creator>Zhang, Heng</creator><creator>Zhuo, Kelei</creator><creator>Lei, Aiwen</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150119</creationdate><title>Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis</title><author>Liu, Jianming ; Zhang, Xin ; Yi, Hong ; Liu, Chao ; Liu, Ren ; Zhang, Heng ; Zhuo, Kelei ; Lei, Aiwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6170-4594a3b8960f775890c17e9427b9ab0814e1778ec3399e2fe8682342759b24ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Catalysts</topic><topic>Copper</topic><topic>copper catalysis</topic><topic>ethyl chloroacetate</topic><topic>Free radicals</topic><topic>Ketones</topic><topic>Methylene</topic><topic>N-heterocycles</topic><topic>Oxidation</topic><topic>Radicals</topic><topic>selective oxidations</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jianming</creatorcontrib><creatorcontrib>Zhang, Xin</creatorcontrib><creatorcontrib>Yi, Hong</creatorcontrib><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Liu, Ren</creatorcontrib><creatorcontrib>Zhang, Heng</creatorcontrib><creatorcontrib>Zhuo, Kelei</creatorcontrib><creatorcontrib>Lei, Aiwen</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jianming</au><au>Zhang, Xin</au><au>Yi, Hong</au><au>Liu, Chao</au><au>Liu, Ren</au><au>Zhang, Heng</au><au>Zhuo, Kelei</au><au>Lei, Aiwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-01-19</date><risdate>2015</risdate><volume>54</volume><issue>4</issue><spage>1261</spage><epage>1265</epage><pages>1261-1265</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N‐heterocyclic compounds and ethyl chloroacetate work synergistically to activate CH bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields.
Molecular oxygen can be used for the selective oxidation of CH bonds of N‐heterocyclic compounds to the corresponding ketones with a copper catalyst and ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25483218</pmid><doi>10.1002/anie.201409580</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Catalysts Copper copper catalysis ethyl chloroacetate Free radicals Ketones Methylene N-heterocycles Oxidation Radicals selective oxidations Transformations |
| title | Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis |
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