Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides

A facile synthesis of α-carbonyl sulfones has been accomplished by the cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides in the presence of CuI and DBU. The reaction employs inexpensive and bench stable sulfonyl hydrazides as a sulfonyl source, and facilitates the migratory insertion w...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2023-02, Vol.21 (5), p.987-993
Hauptverfasser: Sharma, Anup Kumar, Chand, Shiv, Kumar Pandey, Anand, Singh, Krishna Nand
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 993
container_issue 5
container_start_page 987
container_title Organic & biomolecular chemistry
container_volume 21
creator Sharma, Anup Kumar
Chand, Shiv
Kumar Pandey, Anand
Singh, Krishna Nand
description A facile synthesis of α-carbonyl sulfones has been accomplished by the cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides in the presence of CuI and DBU. The reaction employs inexpensive and bench stable sulfonyl hydrazides as a sulfonyl source, and facilitates the migratory insertion with α-aryl-α-diazoesters under mild reaction conditions. Cu-catalyzed cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides is explored to access α-carbonyl sulfones via migratory insertion of Cu-carbene species.
doi_str_mv 10.1039/d2ob02219b
format Article
fullrecord <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_proquest_miscellaneous_2762819899</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2771273508</sourcerecordid><originalsourceid>FETCH-LOGICAL-c267t-6500a0dacd15b6705589f4d93a593f599670cb7a826a741be457bf8d617140383</originalsourceid><addsrcrecordid>eNpdkctOwzAQRS0EolDYsAdFYoOQAn7EcbykpTykSt3AOnJsh6akcfE0Qu1f8SN8E-6DIrEaz_jM1cxchM4IviGYyVtDXYEpJbLYQ0ckESLGnMn93ZviDjoGmGBMpEiTQ9RhaUpElrEj9D5QsIiU1hYgmrvo-yvWyheuWdQRtHXpGgtRC1XzFmnvAGLt2lm9Sl25gpVf1HGIplJLZ2FuPUSf1Xy8bQ4q44XxalkZCyfooFQ12NNt7KLXh8FL_ykejh6f-3fDWNNUzOOUY6ywUdoQXqQCc57JMjGSKS5ZyaUMNV0IldFUiYQUNuGiKDMTViIJZhnroquN7sy7jzYMlU8r0LauVWNdCzkVKc2IzKQM6OU_dOJa34TpAiUIFYzjleD1hlqfwNsyn_lqGlbPCc5XFuT3dNRbW9AL8MVWsi2m1uzQ35sH4HwDeNC73z8P2Q9RqY0g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2771273508</pqid></control><display><type>article</type><title>Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Sharma, Anup Kumar ; Chand, Shiv ; Kumar Pandey, Anand ; Singh, Krishna Nand</creator><creatorcontrib>Sharma, Anup Kumar ; Chand, Shiv ; Kumar Pandey, Anand ; Singh, Krishna Nand</creatorcontrib><description>A facile synthesis of α-carbonyl sulfones has been accomplished by the cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides in the presence of CuI and DBU. The reaction employs inexpensive and bench stable sulfonyl hydrazides as a sulfonyl source, and facilitates the migratory insertion with α-aryl-α-diazoesters under mild reaction conditions. Cu-catalyzed cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides is explored to access α-carbonyl sulfones via migratory insertion of Cu-carbene species.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob02219b</identifier><identifier>PMID: 36617883</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Carbonyl compounds ; Carbonyls ; Cross coupling ; Hydrazides ; Sulfones</subject><ispartof>Organic &amp; biomolecular chemistry, 2023-02, Vol.21 (5), p.987-993</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c267t-6500a0dacd15b6705589f4d93a593f599670cb7a826a741be457bf8d617140383</citedby><cites>FETCH-LOGICAL-c267t-6500a0dacd15b6705589f4d93a593f599670cb7a826a741be457bf8d617140383</cites><orcidid>0000-0001-9147-5463</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36617883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sharma, Anup Kumar</creatorcontrib><creatorcontrib>Chand, Shiv</creatorcontrib><creatorcontrib>Kumar Pandey, Anand</creatorcontrib><creatorcontrib>Singh, Krishna Nand</creatorcontrib><title>Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A facile synthesis of α-carbonyl sulfones has been accomplished by the cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides in the presence of CuI and DBU. The reaction employs inexpensive and bench stable sulfonyl hydrazides as a sulfonyl source, and facilitates the migratory insertion with α-aryl-α-diazoesters under mild reaction conditions. Cu-catalyzed cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides is explored to access α-carbonyl sulfones via migratory insertion of Cu-carbene species.</description><subject>Aromatic compounds</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Cross coupling</subject><subject>Hydrazides</subject><subject>Sulfones</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkctOwzAQRS0EolDYsAdFYoOQAn7EcbykpTykSt3AOnJsh6akcfE0Qu1f8SN8E-6DIrEaz_jM1cxchM4IviGYyVtDXYEpJbLYQ0ckESLGnMn93ZviDjoGmGBMpEiTQ9RhaUpElrEj9D5QsIiU1hYgmrvo-yvWyheuWdQRtHXpGgtRC1XzFmnvAGLt2lm9Sl25gpVf1HGIplJLZ2FuPUSf1Xy8bQ4q44XxalkZCyfooFQ12NNt7KLXh8FL_ykejh6f-3fDWNNUzOOUY6ywUdoQXqQCc57JMjGSKS5ZyaUMNV0IldFUiYQUNuGiKDMTViIJZhnroquN7sy7jzYMlU8r0LauVWNdCzkVKc2IzKQM6OU_dOJa34TpAiUIFYzjleD1hlqfwNsyn_lqGlbPCc5XFuT3dNRbW9AL8MVWsi2m1uzQ35sH4HwDeNC73z8P2Q9RqY0g</recordid><startdate>20230201</startdate><enddate>20230201</enddate><creator>Sharma, Anup Kumar</creator><creator>Chand, Shiv</creator><creator>Kumar Pandey, Anand</creator><creator>Singh, Krishna Nand</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9147-5463</orcidid></search><sort><creationdate>20230201</creationdate><title>Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides</title><author>Sharma, Anup Kumar ; Chand, Shiv ; Kumar Pandey, Anand ; Singh, Krishna Nand</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c267t-6500a0dacd15b6705589f4d93a593f599670cb7a826a741be457bf8d617140383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aromatic compounds</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Cross coupling</topic><topic>Hydrazides</topic><topic>Sulfones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sharma, Anup Kumar</creatorcontrib><creatorcontrib>Chand, Shiv</creatorcontrib><creatorcontrib>Kumar Pandey, Anand</creatorcontrib><creatorcontrib>Singh, Krishna Nand</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sharma, Anup Kumar</au><au>Chand, Shiv</au><au>Kumar Pandey, Anand</au><au>Singh, Krishna Nand</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-02-01</date><risdate>2023</risdate><volume>21</volume><issue>5</issue><spage>987</spage><epage>993</epage><pages>987-993</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A facile synthesis of α-carbonyl sulfones has been accomplished by the cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides in the presence of CuI and DBU. The reaction employs inexpensive and bench stable sulfonyl hydrazides as a sulfonyl source, and facilitates the migratory insertion with α-aryl-α-diazoesters under mild reaction conditions. Cu-catalyzed cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides is explored to access α-carbonyl sulfones via migratory insertion of Cu-carbene species.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36617883</pmid><doi>10.1039/d2ob02219b</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-9147-5463</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2023-02, Vol.21 (5), p.987-993
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_2762819899
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Aromatic compounds
Carbonyl compounds
Carbonyls
Cross coupling
Hydrazides
Sulfones
title Easy access to α-carbonyl sulfones using cross-coupling of α-aryl-α-diazoesters with sulfonyl hydrazides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T23%3A02%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_rsc_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Easy%20access%20to%20%CE%B1-carbonyl%20sulfones%20using%20cross-coupling%20of%20%CE%B1-aryl-%CE%B1-diazoesters%20with%20sulfonyl%20hydrazides&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Sharma,%20Anup%20Kumar&rft.date=2023-02-01&rft.volume=21&rft.issue=5&rft.spage=987&rft.epage=993&rft.pages=987-993&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d2ob02219b&rft_dat=%3Cproquest_rsc_p%3E2771273508%3C/proquest_rsc_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2771273508&rft_id=info:pmid/36617883&rfr_iscdi=true