Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage
The oxidative cleavage of 1,2‐diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6 , Pb(OAc)4 , and KMnO4 , generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly s...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-03, Vol.57 (10), p.2616-2620 |
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| creator | Zhou, Zhong‐zhen Liu, Mingxin Lv, Leiyang Li, Chao‐Jun |
| description | The oxidative cleavage of 1,2‐diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6 , Pb(OAc)4 , and KMnO4 , generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Go silver, go green: The oxidative cleavage of 1,2‐diols is one of the most fundamental organic transformations; however, the stoichiometric oxidants that are generally used (H5IO6, Pb(OAc)4, KMnO4) generate stoichiometric hazardous waste. Such oxidants can be avoided by the highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols with atmospheric oxygen as the sole oxidant (see scheme). |
| doi_str_mv | 10.1002/anie.201711531 |
| format | Article |
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Go silver, go green: The oxidative cleavage of 1,2‐diols is one of the most fundamental organic transformations; however, the stoichiometric oxidants that are generally used (H5IO6, Pb(OAc)4, KMnO4) generate stoichiometric hazardous waste. Such oxidants can be avoided by the highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols with atmospheric oxygen as the sole oxidant (see scheme).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201711531</identifier><identifier>PMID: 29336100</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>1,2-diols ; aerobic oxidative cleavage ; carboxylic acids ; Cleavage ; Diols ; Hazardous wastes ; Oxidants ; Oxidation ; Oxidizing agents ; Silver ; silver catalysis</subject><ispartof>Angewandte Chemie International Edition, 2018-03, Vol.57 (10), p.2616-2620</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4761-fa3797f6457af655410173ee4993ce8596ad387e9ce5a897f9016b2e0c2c0c433</citedby><cites>FETCH-LOGICAL-c4761-fa3797f6457af655410173ee4993ce8596ad387e9ce5a897f9016b2e0c2c0c433</cites><orcidid>0000-0002-3859-8824</orcidid></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.201711531$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201711531$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29336100$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Zhong‐zhen</creatorcontrib><creatorcontrib>Liu, Mingxin</creatorcontrib><creatorcontrib>Lv, Leiyang</creatorcontrib><creatorcontrib>Li, Chao‐Jun</creatorcontrib><title>Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The oxidative cleavage of 1,2‐diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6 , Pb(OAc)4 , and KMnO4 , generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Go silver, go green: The oxidative cleavage of 1,2‐diols is one of the most fundamental organic transformations; however, the stoichiometric oxidants that are generally used (H5IO6, Pb(OAc)4, KMnO4) generate stoichiometric hazardous waste. Such oxidants can be avoided by the highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols with atmospheric oxygen as the sole oxidant (see scheme).</description><subject>1,2-diols</subject><subject>aerobic oxidative cleavage</subject><subject>carboxylic acids</subject><subject>Cleavage</subject><subject>Diols</subject><subject>Hazardous wastes</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Silver</subject><subject>silver catalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0LtOwzAUBmALgbivjCgSS5FI8bHj2B6rcqsEdADEaLnOCTJym5K0hTLxCDwjT4KrcpFYmHyG7_zy-QnZA9oGStmxHXlsMwoSQHBYIZsgGKRcSr4a54zzVCoBG2SraR6jV4rm62SDac7zuL9Jrm58mGHd6h1-vL137cSG-SsWyb0vMMyTzngcvLODgEkH62rgXQJHLMoTX4Wk_-ILO_EzTLoB7cw-4A5ZK21ocPfr3SZ3Z6e33Yv0sn_e63YuU5fJHNLScqllmWdC2jIXIoN4AEfMtOYOldC5LbiSqB0Kq6LUFPIBQ-qYoy4etU1ay9xxXT1NsZmYoW8chmBHWE0bA1ppIRlQEenBH_pYTetR_J1hlCouVMYgqvZSubpqmhpLM6790NZzA9QsijaLos1P0XFh_yt2Ohhi8cO_m41AL8GzDzj_J850rnunv-GfnyCIwg</recordid><startdate>20180301</startdate><enddate>20180301</enddate><creator>Zhou, Zhong‐zhen</creator><creator>Liu, Mingxin</creator><creator>Lv, Leiyang</creator><creator>Li, Chao‐Jun</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3859-8824</orcidid></search><sort><creationdate>20180301</creationdate><title>Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage</title><author>Zhou, Zhong‐zhen ; Liu, Mingxin ; Lv, Leiyang ; Li, Chao‐Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4761-fa3797f6457af655410173ee4993ce8596ad387e9ce5a897f9016b2e0c2c0c433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>1,2-diols</topic><topic>aerobic oxidative cleavage</topic><topic>carboxylic acids</topic><topic>Cleavage</topic><topic>Diols</topic><topic>Hazardous wastes</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Silver</topic><topic>silver catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Zhong‐zhen</creatorcontrib><creatorcontrib>Liu, Mingxin</creatorcontrib><creatorcontrib>Lv, Leiyang</creatorcontrib><creatorcontrib>Li, Chao‐Jun</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Zhong‐zhen</au><au>Liu, Mingxin</au><au>Lv, Leiyang</au><au>Li, Chao‐Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-03-01</date><risdate>2018</risdate><volume>57</volume><issue>10</issue><spage>2616</spage><epage>2620</epage><pages>2616-2620</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The oxidative cleavage of 1,2‐diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6 , Pb(OAc)4 , and KMnO4 , generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Go silver, go green: The oxidative cleavage of 1,2‐diols is one of the most fundamental organic transformations; however, the stoichiometric oxidants that are generally used (H5IO6, Pb(OAc)4, KMnO4) generate stoichiometric hazardous waste. Such oxidants can be avoided by the highly selective silver(I)‐catalyzed oxidative cleavage of 1,2‐diols with atmospheric oxygen as the sole oxidant (see scheme).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29336100</pmid><doi>10.1002/anie.201711531</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3859-8824</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 1,2-diols aerobic oxidative cleavage carboxylic acids Cleavage Diols Hazardous wastes Oxidants Oxidation Oxidizing agents Silver silver catalysis |
| title | Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage |
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