A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride
A metal‐free regioselective synthesis of α‐aryl ketone from corresponding bromohydrin via cooperative cascade effect of [hmim]Br and tetrabutylammonium fluoride under microwave irradiation is reported. Applications of the protocol are illustrated by synthesis of drug intermediates piperonyl‐methyl k...
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| Veröffentlicht in: | Asian journal of organic chemistry 2019-11, Vol.8 (11), p.2017-2022 |
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| container_end_page | 2022 |
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| container_issue | 11 |
| container_start_page | 2017 |
| container_title | Asian journal of organic chemistry |
| container_volume | 8 |
| creator | Thopate, Yogesh Singh, Richa Rastogi, Sumit K. Sinha, Arun K. |
| description | A metal‐free regioselective synthesis of α‐aryl ketone from corresponding bromohydrin via cooperative cascade effect of [hmim]Br and tetrabutylammonium fluoride under microwave irradiation is reported. Applications of the protocol are illustrated by synthesis of drug intermediates piperonyl‐methyl ketone and 2‐tetralone. Interestingly, direct regioselective transformation of epoxide and 1,2‐diol into α‐aryl ketone under neat [hmim]Br has also been realized. Advantages of this method are demonstrated through the recyclability of [hmim]Br‐tetrabutylammonium fluoride catalytic system and gram scalability.
Microwave dinner: A practical and general cooperative cascade effect of an ionic liquid and tetrabutyl ammonium fluoride in the regioselective synthesis of α‐aryl ketones via Wacker‐type oxidation of bromohydrins to ketones is presented. |
| doi_str_mv | 10.1002/ajoc.201900513 |
| format | Article |
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Microwave dinner: A practical and general cooperative cascade effect of an ionic liquid and tetrabutyl ammonium fluoride in the regioselective synthesis of α‐aryl ketones via Wacker‐type oxidation of bromohydrins to ketones is presented.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201900513</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; Bromohydrin ; Cooperative Catalyst ; Fluorides ; Ionic Liquid ; Ionic liquids ; Ketones ; Organic chemistry ; Recyclability ; Regioselectivity ; Synthesis ; Tetrabutylammonium flouride ; α-aryl ketone</subject><ispartof>Asian journal of organic chemistry, 2019-11, Vol.8 (11), p.2017-2022</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-92e5fea4a6810e98a8bbfce9e3ada927e5ae5f12804e3dfd6a39e231d80aa6a03</citedby><cites>FETCH-LOGICAL-c3173-92e5fea4a6810e98a8bbfce9e3ada927e5ae5f12804e3dfd6a39e231d80aa6a03</cites><orcidid>0000-0002-1223-9495</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%2Fajoc.201900513$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201900513$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Thopate, Yogesh</creatorcontrib><creatorcontrib>Singh, Richa</creatorcontrib><creatorcontrib>Rastogi, Sumit K.</creatorcontrib><creatorcontrib>Sinha, Arun K.</creatorcontrib><title>A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride</title><title>Asian journal of organic chemistry</title><description>A metal‐free regioselective synthesis of α‐aryl ketone from corresponding bromohydrin via cooperative cascade effect of [hmim]Br and tetrabutylammonium fluoride under microwave irradiation is reported. Applications of the protocol are illustrated by synthesis of drug intermediates piperonyl‐methyl ketone and 2‐tetralone. Interestingly, direct regioselective transformation of epoxide and 1,2‐diol into α‐aryl ketone under neat [hmim]Br has also been realized. Advantages of this method are demonstrated through the recyclability of [hmim]Br‐tetrabutylammonium fluoride catalytic system and gram scalability.
Microwave dinner: A practical and general cooperative cascade effect of an ionic liquid and tetrabutyl ammonium fluoride in the regioselective synthesis of α‐aryl ketones via Wacker‐type oxidation of bromohydrins to ketones is presented.</description><subject>Aromatic compounds</subject><subject>Bromohydrin</subject><subject>Cooperative Catalyst</subject><subject>Fluorides</subject><subject>Ionic Liquid</subject><subject>Ionic liquids</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>Recyclability</subject><subject>Regioselectivity</subject><subject>Synthesis</subject><subject>Tetrabutylammonium flouride</subject><subject>α-aryl ketone</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc9OwkAQxhujiQS5et7EM7jbbWn3SBoQlATjn3MzdKewpHRht9X05iN49i18ER_CJ3EBg0fnMjOZ3_fN4fO8S0Z7jFL_GlY66_mUCUpDxk-8ls8E74YxC0-PM43OvY61K-oqigTzRcv7GJCxWiyLhjzgQmmLBWaVekECpST3BtySQUEem7JaolWW6Jx8fX6_vQ9MU5A7rHSJltSlREOAJFpv0MDeIAGbgUQyzHNnudNBSSa6VBmZqm2t5P7FE1YG5nXVFLBeu2O9JqOi1kZJvPDOcigsdn5723seDZ-ScXc6u5kkg2k34yziXeFjmCME0I8ZRRFDPJ_nGQrkIEH4EYbgAObHNEAuc9kHLtDnTMYUoA-Ut72rg-_G6G2NtkpXujale5k6LAhiEfK-o3oHKjPaWoN5ujFqDaZJGU13EaS7CNJjBE4gDoJXVWDzD50ObmfJn_YHv0SO7A</recordid><startdate>201911</startdate><enddate>201911</enddate><creator>Thopate, Yogesh</creator><creator>Singh, Richa</creator><creator>Rastogi, Sumit K.</creator><creator>Sinha, Arun K.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1223-9495</orcidid></search><sort><creationdate>201911</creationdate><title>A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride</title><author>Thopate, Yogesh ; Singh, Richa ; Rastogi, Sumit K. ; Sinha, Arun K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-92e5fea4a6810e98a8bbfce9e3ada927e5ae5f12804e3dfd6a39e231d80aa6a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aromatic compounds</topic><topic>Bromohydrin</topic><topic>Cooperative Catalyst</topic><topic>Fluorides</topic><topic>Ionic Liquid</topic><topic>Ionic liquids</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>Recyclability</topic><topic>Regioselectivity</topic><topic>Synthesis</topic><topic>Tetrabutylammonium flouride</topic><topic>α-aryl ketone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thopate, Yogesh</creatorcontrib><creatorcontrib>Singh, Richa</creatorcontrib><creatorcontrib>Rastogi, Sumit K.</creatorcontrib><creatorcontrib>Sinha, Arun K.</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thopate, Yogesh</au><au>Singh, Richa</au><au>Rastogi, Sumit K.</au><au>Sinha, Arun K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2019-11</date><risdate>2019</risdate><volume>8</volume><issue>11</issue><spage>2017</spage><epage>2022</epage><pages>2017-2022</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>A metal‐free regioselective synthesis of α‐aryl ketone from corresponding bromohydrin via cooperative cascade effect of [hmim]Br and tetrabutylammonium fluoride under microwave irradiation is reported. Applications of the protocol are illustrated by synthesis of drug intermediates piperonyl‐methyl ketone and 2‐tetralone. Interestingly, direct regioselective transformation of epoxide and 1,2‐diol into α‐aryl ketone under neat [hmim]Br has also been realized. Advantages of this method are demonstrated through the recyclability of [hmim]Br‐tetrabutylammonium fluoride catalytic system and gram scalability.
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| ispartof | Asian journal of organic chemistry, 2019-11, Vol.8 (11), p.2017-2022 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aromatic compounds Bromohydrin Cooperative Catalyst Fluorides Ionic Liquid Ionic liquids Ketones Organic chemistry Recyclability Regioselectivity Synthesis Tetrabutylammonium flouride α-aryl ketone |
| title | A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride |
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