FeCl3·6H2O-catalyzed selective reduction of allylic halides to alkenes with concomitant oxidation of benzylic alcohols to aldehydes
Iron-catalyzed direct reduction of allylic halides with benzylic alcohol was achieved, providing a new, simple, and efficient method for conducting highly regioselective hydrodehalogenation. This method not only features a readily available reductant, an inexpensive catalyst, simple manipulation, an...
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| Veröffentlicht in: | Science China. Chemistry 2014-02, Vol.57 (2), p.282-288 |
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| container_title | Science China. Chemistry |
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| creator | Zhang, HouCai Liu, RuiTing Zhou, XiGeng |
| description | Iron-catalyzed direct reduction of allylic halides with benzylic alcohol was achieved, providing a new, simple, and efficient method for conducting highly regioselective hydrodehalogenation. This method not only features a readily available reductant, an inexpensive catalyst, simple manipulation, and good tolerance of functional groups including nitriles, nitro, esters, and methoxyl groups, it also has mild reaction conditions and shows complete regioselectivity in that only halides sited at the allylic position are reduced. Alternatively, this method can be applied in the selective transformation of benzylic alcohols to aromatic aldehydes without overoxidation to carboxylic acids. |
| doi_str_mv | 10.1007/s11426-013-5042-2 |
| format | Article |
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Alternatively, this method can be applied in the selective transformation of benzylic alcohols to aromatic aldehydes without overoxidation to carboxylic acids.</description><identifier>ISSN: 1674-7291</identifier><identifier>EISSN: 1869-1870</identifier><identifier>DOI: 10.1007/s11426-013-5042-2</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Alcohols ; Aldehydes ; Carboxylic acids ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Direct reduced iron ; Esters ; Ferric chloride ; Functional groups ; Halides ; Nitriles ; Oxidation ; Reducing agents ; Regioselectivity</subject><ispartof>Science China. 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Chemistry</title><addtitle>Sci. China Chem</addtitle><description>Iron-catalyzed direct reduction of allylic halides with benzylic alcohol was achieved, providing a new, simple, and efficient method for conducting highly regioselective hydrodehalogenation. This method not only features a readily available reductant, an inexpensive catalyst, simple manipulation, and good tolerance of functional groups including nitriles, nitro, esters, and methoxyl groups, it also has mild reaction conditions and shows complete regioselectivity in that only halides sited at the allylic position are reduced. Alternatively, this method can be applied in the selective transformation of benzylic alcohols to aromatic aldehydes without overoxidation to carboxylic acids.</description><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Carboxylic acids</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Direct reduced iron</subject><subject>Esters</subject><subject>Ferric chloride</subject><subject>Functional groups</subject><subject>Halides</subject><subject>Nitriles</subject><subject>Oxidation</subject><subject>Reducing agents</subject><subject>Regioselectivity</subject><issn>1674-7291</issn><issn>1869-1870</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp1kE1LwzAAhosoOOZ-gLeC52i-mmRHGc4Jg130HJI0sZ1ZM5tO7c7-J-_-MjOreDKXvIT3eQNPlp0jeIkg5FcRIYoZgIiAAlIM8FE2QoJNARIcHqfMOAUcT9FpNolxDdMhBGJejLL3uZ158vnBFngFjOqU7_e2zKP11nT1i81bW-5SCk0eXK68731t8kr5urQx70J6erJNiq91V-UmNCZs6k41XR7e6lL9gto2-29SeROq4H_Q0lZ92jnLTpzy0U5-7nH2ML-5ny3AcnV7N7teAoMJwsAxLAylGhkNVamxIUJzTKYM8sI4bAUrptwpwYkqBKXMaOZKrS0jhDshHBlnF8Putg3POxs7uQ67tklfyiRHFKiggqYWGlqmDTG21sltW29U20sE5cG3HHzL5FsefEucGDwwMXWbR9v-Lf8PfQEnv4Ua</recordid><startdate>201402</startdate><enddate>201402</enddate><creator>Zhang, HouCai</creator><creator>Liu, RuiTing</creator><creator>Zhou, XiGeng</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FG</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>M2P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>201402</creationdate><title>FeCl3·6H2O-catalyzed selective reduction of allylic halides to alkenes with concomitant oxidation of benzylic alcohols to aldehydes</title><author>Zhang, HouCai ; Liu, RuiTing ; Zhou, XiGeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2312-f628c44b1cb0adb2c38b72396075cf2e86597fa873a58446cb6fdbbe6337f88f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Carboxylic acids</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Direct reduced iron</topic><topic>Esters</topic><topic>Ferric chloride</topic><topic>Functional groups</topic><topic>Halides</topic><topic>Nitriles</topic><topic>Oxidation</topic><topic>Reducing agents</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, HouCai</creatorcontrib><creatorcontrib>Liu, RuiTing</creatorcontrib><creatorcontrib>Zhou, XiGeng</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Science China. Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, HouCai</au><au>Liu, RuiTing</au><au>Zhou, XiGeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>FeCl3·6H2O-catalyzed selective reduction of allylic halides to alkenes with concomitant oxidation of benzylic alcohols to aldehydes</atitle><jtitle>Science China. Chemistry</jtitle><stitle>Sci. China Chem</stitle><date>2014-02</date><risdate>2014</risdate><volume>57</volume><issue>2</issue><spage>282</spage><epage>288</epage><pages>282-288</pages><issn>1674-7291</issn><eissn>1869-1870</eissn><abstract>Iron-catalyzed direct reduction of allylic halides with benzylic alcohol was achieved, providing a new, simple, and efficient method for conducting highly regioselective hydrodehalogenation. This method not only features a readily available reductant, an inexpensive catalyst, simple manipulation, and good tolerance of functional groups including nitriles, nitro, esters, and methoxyl groups, it also has mild reaction conditions and shows complete regioselectivity in that only halides sited at the allylic position are reduced. Alternatively, this method can be applied in the selective transformation of benzylic alcohols to aromatic aldehydes without overoxidation to carboxylic acids.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s11426-013-5042-2</doi><tpages>7</tpages></addata></record> |
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| ispartof | Science China. Chemistry, 2014-02, Vol.57 (2), p.282-288 |
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| subjects | Alcohols Aldehydes Carboxylic acids Chemistry Chemistry and Materials Science Chemistry/Food Science Direct reduced iron Esters Ferric chloride Functional groups Halides Nitriles Oxidation Reducing agents Regioselectivity |
| title | FeCl3·6H2O-catalyzed selective reduction of allylic halides to alkenes with concomitant oxidation of benzylic alcohols to aldehydes |
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