Mechanochemistry Enabled Construction of Isoxazole Skeleton via CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation
A dehydrohalogenative approach for isoxazole annulation by partnering β‐vinyl halides and α‐nitrocarbonyls under mechanochemical setting was accomplished. This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (
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Veröffentlicht in: | Advanced synthesis & catalysis 2021-11, Vol.363 (21), p.4941-4952 |
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creator | Vadivelu, Murugan Sampath, Sugirdha Muthu, Kesavan Karthikeyan, Kesavan Praveen, Chandrasekar |
description | A dehydrohalogenative approach for isoxazole annulation by partnering β‐vinyl halides and α‐nitrocarbonyls under mechanochemical setting was accomplished. This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles ( |
doi_str_mv | 10.1002/adsc.202100730 |
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This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (<50 nm) and DABCO. The key beneficial aspects of this protocol include: (i) broad substrate scope, (ii) no vigorous work‐up, (iii) short reaction time, (iv) solvent‐free condition, (v) commercial viability of substrates/reagents (vi) good chemical yields and selectivity. The other merit of this chemistry is the ease with which CuO can be recuperated and reused after the reaction with not much drop in catalytic activity for six runs. 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This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (<50 nm) and DABCO. The key beneficial aspects of this protocol include: (i) broad substrate scope, (ii) no vigorous work‐up, (iii) short reaction time, (iv) solvent‐free condition, (v) commercial viability of substrates/reagents (vi) good chemical yields and selectivity. The other merit of this chemistry is the ease with which CuO can be recuperated and reused after the reaction with not much drop in catalytic activity for six runs. With no confinement to β‐vinyl halides, the validated condition is also open to alkynes for isoxazole preparation, thereby establishing the broader utility of the current methodology.</description><subject>Alkynes</subject><subject>Catalysis</subject><subject>Catalytic activity</subject><subject>Chemical reactions</subject><subject>Copper oxides</subject><subject>CuO nanocatalysis</subject><subject>Dehydrohalogenative annulation</subject><subject>Halides</subject><subject>Isoxazoles</subject><subject>Mechanochemistry</subject><subject>Nanoparticles</subject><subject>Organic chemistry</subject><subject>Reaction time</subject><subject>Reagents</subject><subject>Selectivity</subject><subject>Solvent-free conditions</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFUMlOwzAQjRBIlMKVsyXOKXYWOzlWKUulQg-FczR1pjTFtYudFNI_4K9xVVSOnGbezFukFwTXjA4YpdEtVE4OIhp5IGJ6EvQYZ2mYMJ6fHveUngcXzq0oZSITohd8P6FcgjZyievaNbYjdxrmCitSGO1xK5vaaGIWZOzMF-yMQjJ7R4WNv25rIEU7Jc_eYAO2qaVCRwpoQHU7bzHWDdq1l8hWgSUjXHaVNUtQ5g01NPUWyVBr_9tnXAZnC1AOr35nP3i9v3spHsPJ9GFcDCehjJmgoWSQZ3EGcZqKuUiQco5VRtMkWlQ5JrlI45TnjLFMgKAYAwceRxHPc5p4hoz7wc3Bd2PNR4uuKVemtdpHlhFnWcRSxhPPGhxY0hrnLC7Kja3XYLuS0XJfd7mvuzzW7QX5QfBZK-z-YZfD0az40_4A5h6GJA</recordid><startdate>20211109</startdate><enddate>20211109</enddate><creator>Vadivelu, Murugan</creator><creator>Sampath, Sugirdha</creator><creator>Muthu, Kesavan</creator><creator>Karthikeyan, Kesavan</creator><creator>Praveen, Chandrasekar</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-5348-8810</orcidid><orcidid>https://orcid.org/0000-0001-6999-6801</orcidid></search><sort><creationdate>20211109</creationdate><title>Mechanochemistry Enabled Construction of Isoxazole Skeleton via CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation</title><author>Vadivelu, Murugan ; Sampath, Sugirdha ; Muthu, Kesavan ; Karthikeyan, Kesavan ; Praveen, Chandrasekar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3170-c1a9838a3557b74e066ed80542fd9e4975356911187a70e3a6a632269904fd9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkynes</topic><topic>Catalysis</topic><topic>Catalytic activity</topic><topic>Chemical reactions</topic><topic>Copper oxides</topic><topic>CuO nanocatalysis</topic><topic>Dehydrohalogenative annulation</topic><topic>Halides</topic><topic>Isoxazoles</topic><topic>Mechanochemistry</topic><topic>Nanoparticles</topic><topic>Organic chemistry</topic><topic>Reaction time</topic><topic>Reagents</topic><topic>Selectivity</topic><topic>Solvent-free conditions</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vadivelu, Murugan</creatorcontrib><creatorcontrib>Sampath, Sugirdha</creatorcontrib><creatorcontrib>Muthu, Kesavan</creatorcontrib><creatorcontrib>Karthikeyan, Kesavan</creatorcontrib><creatorcontrib>Praveen, Chandrasekar</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vadivelu, Murugan</au><au>Sampath, Sugirdha</au><au>Muthu, Kesavan</au><au>Karthikeyan, Kesavan</au><au>Praveen, Chandrasekar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanochemistry Enabled Construction of Isoxazole Skeleton via CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-11-09</date><risdate>2021</risdate><volume>363</volume><issue>21</issue><spage>4941</spage><epage>4952</epage><pages>4941-4952</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A dehydrohalogenative approach for isoxazole annulation by partnering β‐vinyl halides and α‐nitrocarbonyls under mechanochemical setting was accomplished. This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (<50 nm) and DABCO. The key beneficial aspects of this protocol include: (i) broad substrate scope, (ii) no vigorous work‐up, (iii) short reaction time, (iv) solvent‐free condition, (v) commercial viability of substrates/reagents (vi) good chemical yields and selectivity. The other merit of this chemistry is the ease with which CuO can be recuperated and reused after the reaction with not much drop in catalytic activity for six runs. With no confinement to β‐vinyl halides, the validated condition is also open to alkynes for isoxazole preparation, thereby establishing the broader utility of the current methodology.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202100730</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-5348-8810</orcidid><orcidid>https://orcid.org/0000-0001-6999-6801</orcidid></addata></record> |
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subjects | Alkynes Catalysis Catalytic activity Chemical reactions Copper oxides CuO nanocatalysis Dehydrohalogenative annulation Halides Isoxazoles Mechanochemistry Nanoparticles Organic chemistry Reaction time Reagents Selectivity Solvent-free conditions Substrates |
title | Mechanochemistry Enabled Construction of Isoxazole Skeleton via CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation |
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