Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ket...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2021-05, Vol.86 (9), p.6138-6147
Hauptverfasser: Rahaman, Mizzanoor, Ali, M. Shahnawaz, Jahan, Khorshada, Hinz, Damon, Belayet, Jawad Bin, Majinski, Ryan, Hossain, M. Mahmun
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 6147
container_issue 9
container_start_page 6138
container_title Journal of organic chemistry
container_volume 86
creator Rahaman, Mizzanoor
Ali, M. Shahnawaz
Jahan, Khorshada
Hinz, Damon
Belayet, Jawad Bin
Majinski, Ryan
Hossain, M. Mahmun
description The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.
doi_str_mv 10.1021/acs.joc.0c02972
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2512310335</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2512310335</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-971923a4ec5027fd7b4119fb9dd891b83c94747f4c788d56535bc5ede861423b3</originalsourceid><addsrcrecordid>eNp1kE1Lw0AQhhdRbK2evUmOgqTdzyR7rLF-QEGweg6b3Q1NSbIxuzmkv8y7f8wtqd6cyzDDMy_MA8A1gnMEMVoIaec7I-dQQsxjfAKmiGEYRhzSUzCFEOOQ4IhMwIW1O-iLMXYOJoQklHIUT0G-GRq31a6UwUaaVgemCO6776_GOq2CpSxVmAonqmHvxzctpCtNYw9UKrrcNEMVpKZuTd8oG4hGBSu39buHUuyNkNoJpy_BWSEqq6-OfQY-Hlfv6XO4fn16SZfrUBBCXMhjxDERVEsGcVyoOKcI8SLnSiUc5QmRnMY0LqiMk0SxiBGWS6aVTiJEMcnJDNyOuW1nPnttXVaXVuqqEo02vc0wQ5ggSAjz6GJEZWes7XSRtV1Zi27IEMwOYjMvNvNis6NYf3FzDO_zWqs__tekB-5GYLzsu8b_-m_cD4YZhBU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2512310335</pqid></control><display><type>article</type><title>Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate</title><source>ACS Publications</source><creator>Rahaman, Mizzanoor ; Ali, M. Shahnawaz ; Jahan, Khorshada ; Hinz, Damon ; Belayet, Jawad Bin ; Majinski, Ryan ; Hossain, M. Mahmun</creator><creatorcontrib>Rahaman, Mizzanoor ; Ali, M. Shahnawaz ; Jahan, Khorshada ; Hinz, Damon ; Belayet, Jawad Bin ; Majinski, Ryan ; Hossain, M. Mahmun</creatorcontrib><description>The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.0c02972</identifier><identifier>PMID: 33844917</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2021-05, Vol.86 (9), p.6138-6147</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-971923a4ec5027fd7b4119fb9dd891b83c94747f4c788d56535bc5ede861423b3</citedby><cites>FETCH-LOGICAL-a333t-971923a4ec5027fd7b4119fb9dd891b83c94747f4c788d56535bc5ede861423b3</cites><orcidid>0000-0002-0874-4480</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.0c02972$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.0c02972$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33844917$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rahaman, Mizzanoor</creatorcontrib><creatorcontrib>Ali, M. Shahnawaz</creatorcontrib><creatorcontrib>Jahan, Khorshada</creatorcontrib><creatorcontrib>Hinz, Damon</creatorcontrib><creatorcontrib>Belayet, Jawad Bin</creatorcontrib><creatorcontrib>Majinski, Ryan</creatorcontrib><creatorcontrib>Hossain, M. Mahmun</creatorcontrib><title>Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp1kE1Lw0AQhhdRbK2evUmOgqTdzyR7rLF-QEGweg6b3Q1NSbIxuzmkv8y7f8wtqd6cyzDDMy_MA8A1gnMEMVoIaec7I-dQQsxjfAKmiGEYRhzSUzCFEOOQ4IhMwIW1O-iLMXYOJoQklHIUT0G-GRq31a6UwUaaVgemCO6776_GOq2CpSxVmAonqmHvxzctpCtNYw9UKrrcNEMVpKZuTd8oG4hGBSu39buHUuyNkNoJpy_BWSEqq6-OfQY-Hlfv6XO4fn16SZfrUBBCXMhjxDERVEsGcVyoOKcI8SLnSiUc5QmRnMY0LqiMk0SxiBGWS6aVTiJEMcnJDNyOuW1nPnttXVaXVuqqEo02vc0wQ5ggSAjz6GJEZWes7XSRtV1Zi27IEMwOYjMvNvNis6NYf3FzDO_zWqs__tekB-5GYLzsu8b_-m_cD4YZhBU</recordid><startdate>20210507</startdate><enddate>20210507</enddate><creator>Rahaman, Mizzanoor</creator><creator>Ali, M. Shahnawaz</creator><creator>Jahan, Khorshada</creator><creator>Hinz, Damon</creator><creator>Belayet, Jawad Bin</creator><creator>Majinski, Ryan</creator><creator>Hossain, M. Mahmun</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0874-4480</orcidid></search><sort><creationdate>20210507</creationdate><title>Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate</title><author>Rahaman, Mizzanoor ; Ali, M. Shahnawaz ; Jahan, Khorshada ; Hinz, Damon ; Belayet, Jawad Bin ; Majinski, Ryan ; Hossain, M. Mahmun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-971923a4ec5027fd7b4119fb9dd891b83c94747f4c788d56535bc5ede861423b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rahaman, Mizzanoor</creatorcontrib><creatorcontrib>Ali, M. Shahnawaz</creatorcontrib><creatorcontrib>Jahan, Khorshada</creatorcontrib><creatorcontrib>Hinz, Damon</creatorcontrib><creatorcontrib>Belayet, Jawad Bin</creatorcontrib><creatorcontrib>Majinski, Ryan</creatorcontrib><creatorcontrib>Hossain, M. Mahmun</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rahaman, Mizzanoor</au><au>Ali, M. Shahnawaz</au><au>Jahan, Khorshada</au><au>Hinz, Damon</au><au>Belayet, Jawad Bin</au><au>Majinski, Ryan</au><au>Hossain, M. Mahmun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2021-05-07</date><risdate>2021</risdate><volume>86</volume><issue>9</issue><spage>6138</spage><epage>6147</epage><pages>6138-6147</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33844917</pmid><doi>10.1021/acs.joc.0c02972</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-0874-4480</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2021-05, Vol.86 (9), p.6138-6147
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2512310335
source ACS Publications
title Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T16%3A36%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthetic%20Scope%20of%20Br%C3%B8nsted%20Acid-Catalyzed%20Reactions%20of%20Carbonyl%20Compounds%20and%20Ethyl%20Diazoacetate&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Rahaman,%20Mizzanoor&rft.date=2021-05-07&rft.volume=86&rft.issue=9&rft.spage=6138&rft.epage=6147&rft.pages=6138-6147&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.0c02972&rft_dat=%3Cproquest_cross%3E2512310335%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2512310335&rft_id=info:pmid/33844917&rfr_iscdi=true