Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation

Herein, we report Rh(III) catalyzed aldehydic or aryl C-H alkylation C-C bond activation of cyclopropanols, facilitating the synthesis of β-functionalized ketones. The protocol employs cyclopropanol as the alkylating agent with 2-aminobenzaldehyde or aniline derivatives to access a variety of unsymm...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2024-09, Vol.60 (76), p.10576-10579
Hauptverfasser:	Dash, Om Prakash, Garg, Divya, Volla, Chandra M R
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Aniline Aromatic compounds Chemical synthesis Covalent bonds Diketones Ketones Natural products Substrates
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	10579
container_issue	76
container_start_page	10576
container_title	Chemical communications (Cambridge, England)
container_volume	60
creator	Dash, Om Prakash Garg, Divya Volla, Chandra M R
description	Herein, we report Rh(III) catalyzed aldehydic or aryl C-H alkylation C-C bond activation of cyclopropanols, facilitating the synthesis of β-functionalized ketones. The protocol employs cyclopropanol as the alkylating agent with 2-aminobenzaldehyde or aniline derivatives to access a variety of unsymmetrical 1,4-diketones or β-aryl ketones, respectively. The practicality of these transformations is showcased through the modification of natural products, gram-scale synthesis, broad substrate scope and postfunctionalizations.
doi_str_mv	10.1039/d4cc03797a
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3100917697</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3106954135</sourcerecordid><originalsourceid>FETCH-LOGICAL-c204t-16ca2f2a3ceee16af14c44ed96291434a3cadc1edbdbd7f11816d95a233fe5ee3</originalsourceid><addsrcrecordid>eNpdkFtLwzAUgIMobk5f_AFS8GUKcUmTtsvjqJcNBoIo-Fay5JR1Zs1s2kn99abb9MGch9y-czjnQ-iSkjtKmBhprhRhiUjkEepTFnMc8fH7cXeOBE4Yj3rozLkV8YtG41PUYyJkLGa0j9TLcjibzW6wkrU07TfoQBoNy1YXKpClv1WtCVI89c8frZF1Ycvgq6iXgWqVsZvKbmRpjQu2heywUYrTYGG7RFUX2x1_jk5yaRxcHPYBent8eE2neP78NEsnc6xCwmtMYyXDPJRMAQCNZU654hy0iENBOeP-Q2pFQS98JDmlYxprEUk_Sg4RABug4b6u7-qzAVdn68IpMEaWYBuXMUqIoEksEo9e_0NXtqlK311HxSLi3p2nbveUqqxzFeTZpirW3khGSdapz-55mu7UTzx8dSjZLNag_9Bf1-wHckd9sg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3106954135</pqid></control><display><type>article</type><title>Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Dash, Om Prakash ; Garg, Divya ; Volla, Chandra M R</creator><creatorcontrib>Dash, Om Prakash ; Garg, Divya ; Volla, Chandra M R</creatorcontrib><description>Herein, we report Rh(III) catalyzed aldehydic or aryl C-H alkylation C-C bond activation of cyclopropanols, facilitating the synthesis of β-functionalized ketones. The protocol employs cyclopropanol as the alkylating agent with 2-aminobenzaldehyde or aniline derivatives to access a variety of unsymmetrical 1,4-diketones or β-aryl ketones, respectively. The practicality of these transformations is showcased through the modification of natural products, gram-scale synthesis, broad substrate scope and postfunctionalizations.</description><identifier>ISSN: 1359-7345</identifier><identifier>ISSN: 1364-548X</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d4cc03797a</identifier><identifier>PMID: 39233631</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkylation ; Aniline ; Aromatic compounds ; Chemical synthesis ; Covalent bonds ; Diketones ; Ketones ; Natural products ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2024-09, Vol.60 (76), p.10576-10579</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c204t-16ca2f2a3ceee16af14c44ed96291434a3cadc1edbdbd7f11816d95a233fe5ee3</cites><orcidid>0000-0002-8497-1538</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39233631$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dash, Om Prakash</creatorcontrib><creatorcontrib>Garg, Divya</creatorcontrib><creatorcontrib>Volla, Chandra M R</creatorcontrib><title>Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Herein, we report Rh(III) catalyzed aldehydic or aryl C-H alkylation C-C bond activation of cyclopropanols, facilitating the synthesis of β-functionalized ketones. The protocol employs cyclopropanol as the alkylating agent with 2-aminobenzaldehyde or aniline derivatives to access a variety of unsymmetrical 1,4-diketones or β-aryl ketones, respectively. The practicality of these transformations is showcased through the modification of natural products, gram-scale synthesis, broad substrate scope and postfunctionalizations.</description><subject>Alkylation</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>Chemical synthesis</subject><subject>Covalent bonds</subject><subject>Diketones</subject><subject>Ketones</subject><subject>Natural products</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkFtLwzAUgIMobk5f_AFS8GUKcUmTtsvjqJcNBoIo-Fay5JR1Zs1s2kn99abb9MGch9y-czjnQ-iSkjtKmBhprhRhiUjkEepTFnMc8fH7cXeOBE4Yj3rozLkV8YtG41PUYyJkLGa0j9TLcjibzW6wkrU07TfoQBoNy1YXKpClv1WtCVI89c8frZF1Ycvgq6iXgWqVsZvKbmRpjQu2heywUYrTYGG7RFUX2x1_jk5yaRxcHPYBent8eE2neP78NEsnc6xCwmtMYyXDPJRMAQCNZU654hy0iENBOeP-Q2pFQS98JDmlYxprEUk_Sg4RABug4b6u7-qzAVdn68IpMEaWYBuXMUqIoEksEo9e_0NXtqlK311HxSLi3p2nbveUqqxzFeTZpirW3khGSdapz-55mu7UTzx8dSjZLNag_9Bf1-wHckd9sg</recordid><startdate>20240920</startdate><enddate>20240920</enddate><creator>Dash, Om Prakash</creator><creator>Garg, Divya</creator><creator>Volla, Chandra M R</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8497-1538</orcidid></search><sort><creationdate>20240920</creationdate><title>Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation</title><author>Dash, Om Prakash ; Garg, Divya ; Volla, Chandra M R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c204t-16ca2f2a3ceee16af14c44ed96291434a3cadc1edbdbd7f11816d95a233fe5ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkylation</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>Chemical synthesis</topic><topic>Covalent bonds</topic><topic>Diketones</topic><topic>Ketones</topic><topic>Natural products</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dash, Om Prakash</creatorcontrib><creatorcontrib>Garg, Divya</creatorcontrib><creatorcontrib>Volla, Chandra M R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dash, Om Prakash</au><au>Garg, Divya</au><au>Volla, Chandra M R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-09-20</date><risdate>2024</risdate><volume>60</volume><issue>76</issue><spage>10576</spage><epage>10579</epage><pages>10576-10579</pages><issn>1359-7345</issn><issn>1364-548X</issn><eissn>1364-548X</eissn><abstract>Herein, we report Rh(III) catalyzed aldehydic or aryl C-H alkylation C-C bond activation of cyclopropanols, facilitating the synthesis of β-functionalized ketones. The protocol employs cyclopropanol as the alkylating agent with 2-aminobenzaldehyde or aniline derivatives to access a variety of unsymmetrical 1,4-diketones or β-aryl ketones, respectively. The practicality of these transformations is showcased through the modification of natural products, gram-scale synthesis, broad substrate scope and postfunctionalizations.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39233631</pmid><doi>10.1039/d4cc03797a</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-8497-1538</orcidid></addata></record>
fulltext	fulltext
identifier	ISSN: 1359-7345
ispartof	Chemical communications (Cambridge, England), 2024-09, Vol.60 (76), p.10576-10579
issn	1359-7345 1364-548X 1364-548X
language	eng
recordid	cdi_proquest_miscellaneous_3100917697
source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Alkylation Aniline Aromatic compounds Chemical synthesis Covalent bonds Diketones Ketones Natural products Substrates
title	Rh(III)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T20%3A38%3A50IST&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=Rh(III)-catalyzed%20aldehydic%20and%20aryl%20C-H%20alkylation%20with%20cyclopropanols%20via%20C-H/C-C%20bond%20activation&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Dash,%20Om%20Prakash&rft.date=2024-09-20&rft.volume=60&rft.issue=76&rft.spage=10576&rft.epage=10579&rft.pages=10576-10579&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d4cc03797a&rft_dat=%3Cproquest_cross%3E3106954135%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=3106954135&rft_id=info:pmid/39233631&rfr_iscdi=true