Additive‐Free Synthesis of Trifluoromethylated Spiro Cyclopropanes and Their Transformation into Trifluoromethylated Building Blocks
An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. This mild protocol displays good functional group tolerance to deliver trifluoromethylated cyclopropanes in high yields. The synthetic potential of the strategy has been explo...
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| Veröffentlicht in: | Asian journal of organic chemistry 2021-06, Vol.10 (6), p.1536-1541 |
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| container_title | Asian journal of organic chemistry |
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| creator | Kumar, Anuj Jamali, Muhammad Fahad Thomas, Shilpa Ahamad, Shakir Kant, Ruchir Mohanan, Kishor |
| description | An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. This mild protocol displays good functional group tolerance to deliver trifluoromethylated cyclopropanes in high yields. The synthetic potential of the strategy has been explored by the expedient synthesis of CF3‐containing spiro‐pyrrolines and organo‐sulfur scaffolds. Moreover, this protocol provides an interesting substrate for regioselective Friedel‐Crafts alkylation.
An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. The synthetic potential of the strategy has been explored by transforming these novel cyclopropanes into various CF3‐containing structural units. |
| doi_str_mv | 10.1002/ajoc.202100207 |
| format | Article |
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An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. The synthetic potential of the strategy has been explored by transforming these novel cyclopropanes into various CF3‐containing structural units.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202100207</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>1,3-dipolar cycloaddition ; Alkylation ; Friedel-Crafts alkylation ; Functional groups ; Organic chemistry ; Organic compounds ; Spiro-pyrroline ; Substrates ; Synthesis ; Trifluorodiazoethane ; Trifluoromethylcyclopropanes</subject><ispartof>Asian journal of organic chemistry, 2021-06, Vol.10 (6), p.1536-1541</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3177-20a803e2608bc53a2cd607693ef033434b67978a7bbbfc0445d87d927fbb3d943</citedby><cites>FETCH-LOGICAL-c3177-20a803e2608bc53a2cd607693ef033434b67978a7bbbfc0445d87d927fbb3d943</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%2Fajoc.202100207$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202100207$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Kumar, Anuj</creatorcontrib><creatorcontrib>Jamali, Muhammad Fahad</creatorcontrib><creatorcontrib>Thomas, Shilpa</creatorcontrib><creatorcontrib>Ahamad, Shakir</creatorcontrib><creatorcontrib>Kant, Ruchir</creatorcontrib><creatorcontrib>Mohanan, Kishor</creatorcontrib><title>Additive‐Free Synthesis of Trifluoromethylated Spiro Cyclopropanes and Their Transformation into Trifluoromethylated Building Blocks</title><title>Asian journal of organic chemistry</title><description>An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. This mild protocol displays good functional group tolerance to deliver trifluoromethylated cyclopropanes in high yields. The synthetic potential of the strategy has been explored by the expedient synthesis of CF3‐containing spiro‐pyrrolines and organo‐sulfur scaffolds. Moreover, this protocol provides an interesting substrate for regioselective Friedel‐Crafts alkylation.
An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. The synthetic potential of the strategy has been explored by transforming these novel cyclopropanes into various CF3‐containing structural units.</description><subject>1,3-dipolar cycloaddition</subject><subject>Alkylation</subject><subject>Friedel-Crafts alkylation</subject><subject>Functional groups</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Spiro-pyrroline</subject><subject>Substrates</subject><subject>Synthesis</subject><subject>Trifluorodiazoethane</subject><subject>Trifluoromethylcyclopropanes</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkD9PwzAQxSMEElXpymyJOcWxkzge24jyR5U6tMyWE9vUJbWDnYCyMTHzGfkkJCoqCxK33J30fu9OLwguIziNIETXfGfLKYJoWCA5CUYoojhMsig5Pc6QnAcT73ewL0JohOgo-JgJoRv9Kr_ePxdOSrDuTLOVXntgFdg4rarWOruXzbareCMFWNfaWZB3ZWVrZ2tupAfcCLDZSu16ghuvrNvzRlsDtGnsny7zVldCmycwr2z57C-CM8UrLyc_fRw8Lm42-V24XN3e57NlWOKIkBBBnkEsUQqzokwwR6VIIUkplgpiHOO4SAklGSdFUagSxnEiMiIoIqoosKAxHgdXB9_-9ZdW-obtbOtMf5KhBNMkGvheNT2oSme9d1Kx2uk9dx2LIBsSZkPc7Bh3D9AD8KYr2f2jZrOHVf7LfgNGI4ee</recordid><startdate>202106</startdate><enddate>202106</enddate><creator>Kumar, Anuj</creator><creator>Jamali, Muhammad Fahad</creator><creator>Thomas, Shilpa</creator><creator>Ahamad, Shakir</creator><creator>Kant, Ruchir</creator><creator>Mohanan, Kishor</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202106</creationdate><title>Additive‐Free Synthesis of Trifluoromethylated Spiro Cyclopropanes and Their Transformation into Trifluoromethylated Building Blocks</title><author>Kumar, Anuj ; Jamali, Muhammad Fahad ; Thomas, Shilpa ; Ahamad, Shakir ; Kant, Ruchir ; Mohanan, Kishor</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3177-20a803e2608bc53a2cd607693ef033434b67978a7bbbfc0445d87d927fbb3d943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>1,3-dipolar cycloaddition</topic><topic>Alkylation</topic><topic>Friedel-Crafts alkylation</topic><topic>Functional groups</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Spiro-pyrroline</topic><topic>Substrates</topic><topic>Synthesis</topic><topic>Trifluorodiazoethane</topic><topic>Trifluoromethylcyclopropanes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Anuj</creatorcontrib><creatorcontrib>Jamali, Muhammad Fahad</creatorcontrib><creatorcontrib>Thomas, Shilpa</creatorcontrib><creatorcontrib>Ahamad, Shakir</creatorcontrib><creatorcontrib>Kant, Ruchir</creatorcontrib><creatorcontrib>Mohanan, Kishor</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Anuj</au><au>Jamali, Muhammad Fahad</au><au>Thomas, Shilpa</au><au>Ahamad, Shakir</au><au>Kant, Ruchir</au><au>Mohanan, Kishor</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Additive‐Free Synthesis of Trifluoromethylated Spiro Cyclopropanes and Their Transformation into Trifluoromethylated Building Blocks</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2021-06</date><risdate>2021</risdate><volume>10</volume><issue>6</issue><spage>1536</spage><epage>1541</epage><pages>1536-1541</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. This mild protocol displays good functional group tolerance to deliver trifluoromethylated cyclopropanes in high yields. The synthetic potential of the strategy has been explored by the expedient synthesis of CF3‐containing spiro‐pyrrolines and organo‐sulfur scaffolds. Moreover, this protocol provides an interesting substrate for regioselective Friedel‐Crafts alkylation.
An efficient additive‐free cyclopropanation of 2‐arylideneindane‐1,3‐dione has been realized employing trifluorodiazoethane. The synthetic potential of the strategy has been explored by transforming these novel cyclopropanes into various CF3‐containing structural units.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202100207</doi><tpages>6</tpages></addata></record> |
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| subjects | 1,3-dipolar cycloaddition Alkylation Friedel-Crafts alkylation Functional groups Organic chemistry Organic compounds Spiro-pyrroline Substrates Synthesis Trifluorodiazoethane Trifluoromethylcyclopropanes |
| title | Additive‐Free Synthesis of Trifluoromethylated Spiro Cyclopropanes and Their Transformation into Trifluoromethylated Building Blocks |
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