Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors
We present a Lewis acid catalyzed nucleophilic ring‐opening of donor‐acceptor cyclopropanes and ‐butanes by sydnones, utilizing their respective 1,3‐ and 1,4‐reactivity. The same conditions can be applied for the addition of sydnones to Michael acceptors. We propose a Friedel‐Crafts like mechanism....
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| Veröffentlicht in: | European journal of organic chemistry 2021-03, Vol.2021 (10), p.1603-1606 |
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| container_issue | 10 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Ahlburg, Nils L. Freese, Tyll Kolb, Simon Mummel, Sebastian Schmidt, Andreas Werz, Daniel B. |
| description | We present a Lewis acid catalyzed nucleophilic ring‐opening of donor‐acceptor cyclopropanes and ‐butanes by sydnones, utilizing their respective 1,3‐ and 1,4‐reactivity. The same conditions can be applied for the addition of sydnones to Michael acceptors. We propose a Friedel‐Crafts like mechanism. The reaction provides a rare, low‐temperature, transition metal‐free, and functional group tolerant protocol for the late‐stage functionalization of these mesoionic compounds of emerging importance in catalysis and bio‐orthogonal chemistry.
We present an easy one‐fits‐all, transition metal‐free protocol for a Friedel‐Crafts type functionalization of sydnones with donor‐acceptor cyclopropanes, cyclobutanes, and Michael acceptors. Yields range from moderate to excellent and are indifferent to scale‐up. The products can be of use to the emerging field of bio‐orthogonal sydnone chemistry. |
| doi_str_mv | 10.1002/ejoc.202100070 |
| format | Article |
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We present an easy one‐fits‐all, transition metal‐free protocol for a Friedel‐Crafts type functionalization of sydnones with donor‐acceptor cyclopropanes, cyclobutanes, and Michael acceptors. Yields range from moderate to excellent and are indifferent to scale‐up. The products can be of use to the emerging field of bio‐orthogonal sydnone chemistry.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100070</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Butanes ; Donor-acceptor systems ; Functional groups ; Lewis acid ; Lewis acids ; Michael acceptor ; Organic compounds ; Small ring systems ; Sydnone ; Transition metals</subject><ispartof>European journal of organic chemistry, 2021-03, Vol.2021 (10), p.1603-1606</ispartof><rights>2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH</rights><rights>2021. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3570-1af34016cec692aeb48bf98d47f14ea1f2d0e55d5aee11ee15281d46573a60623</citedby><cites>FETCH-LOGICAL-c3570-1af34016cec692aeb48bf98d47f14ea1f2d0e55d5aee11ee15281d46573a60623</cites><orcidid>0000-0002-3973-2212</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%2Fejoc.202100070$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100070$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Ahlburg, Nils L.</creatorcontrib><creatorcontrib>Freese, Tyll</creatorcontrib><creatorcontrib>Kolb, Simon</creatorcontrib><creatorcontrib>Mummel, Sebastian</creatorcontrib><creatorcontrib>Schmidt, Andreas</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><title>Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors</title><title>European journal of organic chemistry</title><description>We present a Lewis acid catalyzed nucleophilic ring‐opening of donor‐acceptor cyclopropanes and ‐butanes by sydnones, utilizing their respective 1,3‐ and 1,4‐reactivity. The same conditions can be applied for the addition of sydnones to Michael acceptors. We propose a Friedel‐Crafts like mechanism. The reaction provides a rare, low‐temperature, transition metal‐free, and functional group tolerant protocol for the late‐stage functionalization of these mesoionic compounds of emerging importance in catalysis and bio‐orthogonal chemistry.
We present an easy one‐fits‐all, transition metal‐free protocol for a Friedel‐Crafts type functionalization of sydnones with donor‐acceptor cyclopropanes, cyclobutanes, and Michael acceptors. Yields range from moderate to excellent and are indifferent to scale‐up. The products can be of use to the emerging field of bio‐orthogonal sydnone chemistry.</description><subject>Butanes</subject><subject>Donor-acceptor systems</subject><subject>Functional groups</subject><subject>Lewis acid</subject><subject>Lewis acids</subject><subject>Michael acceptor</subject><subject>Organic compounds</subject><subject>Small ring systems</subject><subject>Sydnone</subject><subject>Transition metals</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkMtOwzAQRS0EEqWwZR2JLSljx3HiZRUoDxV1AUjsLNex1VQhDnaqKqz4BL6RL8FVeCxZjGaudO5o5iJ0imGCAciFXls1IUCCgAz20AgD5zEwDvthpgmNMU-eD9GR9-uAcMbwCJnZplFdZRtZV29yN0TWRA992dhG-2hbdavo0jbWfb5_TJXSbWddVPSqtq2zrQzM-SCXm25Qsimj-0qtpK6jH4c_RgdG1l6ffPcxeppdPRY38XxxfVtM57FK0gxiLE1CATOlFeNE6iXNl4bnJc0MplpiQ0rQaVqmUmuMQ6UkxyVlaZZIBowkY3Q27A3XvW6078Tablx4zguShpByIJQFajJQylnvnTaiddWLdL3AIHZZil2W4jfLYOCDYVvVuv-HFld3i-LP-wVzWHpt</recordid><startdate>20210312</startdate><enddate>20210312</enddate><creator>Ahlburg, Nils L.</creator><creator>Freese, Tyll</creator><creator>Kolb, Simon</creator><creator>Mummel, Sebastian</creator><creator>Schmidt, Andreas</creator><creator>Werz, Daniel B.</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3973-2212</orcidid></search><sort><creationdate>20210312</creationdate><title>Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors</title><author>Ahlburg, Nils L. ; Freese, Tyll ; Kolb, Simon ; Mummel, Sebastian ; Schmidt, Andreas ; Werz, Daniel B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3570-1af34016cec692aeb48bf98d47f14ea1f2d0e55d5aee11ee15281d46573a60623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Butanes</topic><topic>Donor-acceptor systems</topic><topic>Functional groups</topic><topic>Lewis acid</topic><topic>Lewis acids</topic><topic>Michael acceptor</topic><topic>Organic compounds</topic><topic>Small ring systems</topic><topic>Sydnone</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahlburg, Nils L.</creatorcontrib><creatorcontrib>Freese, Tyll</creatorcontrib><creatorcontrib>Kolb, Simon</creatorcontrib><creatorcontrib>Mummel, Sebastian</creatorcontrib><creatorcontrib>Schmidt, Andreas</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><collection>Wiley Open Access</collection><collection>Wiley Online Library Free Content</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahlburg, Nils L.</au><au>Freese, Tyll</au><au>Kolb, Simon</au><au>Mummel, Sebastian</au><au>Schmidt, Andreas</au><au>Werz, Daniel B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-03-12</date><risdate>2021</risdate><volume>2021</volume><issue>10</issue><spage>1603</spage><epage>1606</epage><pages>1603-1606</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We present a Lewis acid catalyzed nucleophilic ring‐opening of donor‐acceptor cyclopropanes and ‐butanes by sydnones, utilizing their respective 1,3‐ and 1,4‐reactivity. The same conditions can be applied for the addition of sydnones to Michael acceptors. We propose a Friedel‐Crafts like mechanism. The reaction provides a rare, low‐temperature, transition metal‐free, and functional group tolerant protocol for the late‐stage functionalization of these mesoionic compounds of emerging importance in catalysis and bio‐orthogonal chemistry.
We present an easy one‐fits‐all, transition metal‐free protocol for a Friedel‐Crafts type functionalization of sydnones with donor‐acceptor cyclopropanes, cyclobutanes, and Michael acceptors. Yields range from moderate to excellent and are indifferent to scale‐up. The products can be of use to the emerging field of bio‐orthogonal sydnone chemistry.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100070</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-3973-2212</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Butanes Donor-acceptor systems Functional groups Lewis acid Lewis acids Michael acceptor Organic compounds Small ring systems Sydnone Transition metals |
| title | Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors |
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