Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes

Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes

A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-09, Vol.58 (71), p.9926-9929
Hauptverfasser: Yang, Ze-ren, Zhang, Bo, Long, Yong-jie, Shi, Min
Format: Artikel
Sprache:eng
Schlagworte:
Deuterium
Diesters
Indoles
Palladium
Phosphines
Pyrroles
Reaction mechanisms
Reagents
Substrates
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9929
container_issue 71
container_start_page 9926
container_title Chemical communications (Cambridge, England)
container_volume 58
creator Yang, Ze-ren
Zhang, Bo
Long, Yong-jie
Shi, Min
description A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction is one of the few examples of hydroamination at electron-rich allene's β-position. A plausible reaction mechanism has also been proposed through a zwitterionic π-propargyl N -palladium species according to the previous work and the obtained deuterium labeling experimental result. A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) via palladium and Lewis acid catalyzed hydroamination of vinylidenecyclopropane-diesters (VDCP-diesters) under mild conditions.
doi_str_mv 10.1039/d2cc03635e
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2708676145</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2703983910</sourcerecordid><originalsourceid>FETCH-LOGICAL-c314t-79877a7714e1cc8234e23ed9857a5abe9e7138e0009c13cafadf83046ea3b2833</originalsourceid><addsrcrecordid>eNpdkU9LxDAQxYMoqKsX70LAiwjVpmmb1Jus6x8Q9KDgrYzJlI20SU26Sv0Ofmezrqg4l0zgx5uZ9wjZY-kxS3l1ojOlUl7yAtfIFuNlnhS5fFxf9kWVCJ4Xm2Q7hOc0FivkFvm4g7YFbRZdomCAdnxHTeej9g46Y2EwzlLX0Fdjx9ZotKhG1breux4sJtpgGNDTNzPMaT9671oMFKymxuplfxo_FPrIg5rTwVF4B_Cui8JqJfpXL-yQjQbagLvf74Q8XMzup1fJze3l9fTsJlGc5UMiKikECMFyZErJjOeYcdSVLAQU8IQVCsYlxhsrxbiCBnQjeZqXCPwpk5xPyOFKNw5-WcQb6s4EhdEJi24R6kxEMyWvoqcTcvAPfXYLb-N2S0qWomR5EamjFaW8C8FjU_fedODHmqX1Mpn6PJtOv5KZRXh_Bfugfrjf5Pgn6HmOmQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2708676145</pqid></control><display><type>article</type><title>Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes</title><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Yang, Ze-ren ; Zhang, Bo ; Long, Yong-jie ; Shi, Min</creator><creatorcontrib>Yang, Ze-ren ; Zhang, Bo ; Long, Yong-jie ; Shi, Min</creatorcontrib><description>A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction is one of the few examples of hydroamination at electron-rich allene's β-position. A plausible reaction mechanism has also been proposed through a zwitterionic π-propargyl N -palladium species according to the previous work and the obtained deuterium labeling experimental result. A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) via palladium and Lewis acid catalyzed hydroamination of vinylidenecyclopropane-diesters (VDCP-diesters) under mild conditions.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc03635e</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Deuterium ; Diesters ; Indoles ; Palladium ; Phosphines ; Pyrroles ; Reaction mechanisms ; Reagents ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2022-09, Vol.58 (71), p.9926-9929</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c314t-79877a7714e1cc8234e23ed9857a5abe9e7138e0009c13cafadf83046ea3b2833</citedby><cites>FETCH-LOGICAL-c314t-79877a7714e1cc8234e23ed9857a5abe9e7138e0009c13cafadf83046ea3b2833</cites><orcidid>0000-0003-0016-5211</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27928,27929</link.rule.ids></links><search><creatorcontrib>Yang, Ze-ren</creatorcontrib><creatorcontrib>Zhang, Bo</creatorcontrib><creatorcontrib>Long, Yong-jie</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><title>Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes</title><title>Chemical communications (Cambridge, England)</title><description>A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction is one of the few examples of hydroamination at electron-rich allene's β-position. A plausible reaction mechanism has also been proposed through a zwitterionic π-propargyl N -palladium species according to the previous work and the obtained deuterium labeling experimental result. A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) via palladium and Lewis acid catalyzed hydroamination of vinylidenecyclopropane-diesters (VDCP-diesters) under mild conditions.</description><subject>Deuterium</subject><subject>Diesters</subject><subject>Indoles</subject><subject>Palladium</subject><subject>Phosphines</subject><subject>Pyrroles</subject><subject>Reaction mechanisms</subject><subject>Reagents</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkU9LxDAQxYMoqKsX70LAiwjVpmmb1Jus6x8Q9KDgrYzJlI20SU26Sv0Ofmezrqg4l0zgx5uZ9wjZY-kxS3l1ojOlUl7yAtfIFuNlnhS5fFxf9kWVCJ4Xm2Q7hOc0FivkFvm4g7YFbRZdomCAdnxHTeej9g46Y2EwzlLX0Fdjx9ZotKhG1breux4sJtpgGNDTNzPMaT9671oMFKymxuplfxo_FPrIg5rTwVF4B_Cui8JqJfpXL-yQjQbagLvf74Q8XMzup1fJze3l9fTsJlGc5UMiKikECMFyZErJjOeYcdSVLAQU8IQVCsYlxhsrxbiCBnQjeZqXCPwpk5xPyOFKNw5-WcQb6s4EhdEJi24R6kxEMyWvoqcTcvAPfXYLb-N2S0qWomR5EamjFaW8C8FjU_fedODHmqX1Mpn6PJtOv5KZRXh_Bfugfrjf5Pgn6HmOmQ</recordid><startdate>20220901</startdate><enddate>20220901</enddate><creator>Yang, Ze-ren</creator><creator>Zhang, Bo</creator><creator>Long, Yong-jie</creator><creator>Shi, Min</creator><general>Royal Society of Chemistry</general><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/0000-0003-0016-5211</orcidid></search><sort><creationdate>20220901</creationdate><title>Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes</title><author>Yang, Ze-ren ; Zhang, Bo ; Long, Yong-jie ; Shi, Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c314t-79877a7714e1cc8234e23ed9857a5abe9e7138e0009c13cafadf83046ea3b2833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Deuterium</topic><topic>Diesters</topic><topic>Indoles</topic><topic>Palladium</topic><topic>Phosphines</topic><topic>Pyrroles</topic><topic>Reaction mechanisms</topic><topic>Reagents</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Ze-ren</creatorcontrib><creatorcontrib>Zhang, Bo</creatorcontrib><creatorcontrib>Long, Yong-jie</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><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>Yang, Ze-ren</au><au>Zhang, Bo</au><au>Long, Yong-jie</au><au>Shi, Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2022-09-01</date><risdate>2022</risdate><volume>58</volume><issue>71</issue><spage>9926</spage><epage>9929</epage><pages>9926-9929</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) has been disclosed in this paper by using pyrrole or indole derivatives as nucleophilic reagents to react with vinylidenecyclopropane-diesters (VDCP-diesters) in the presence of a Pd catalyst, a phosphine ligand and a base under mild conditions in up to 98% yield with a reasonable substrate scope. This reaction is one of the few examples of hydroamination at electron-rich allene's β-position. A plausible reaction mechanism has also been proposed through a zwitterionic π-propargyl N -palladium species according to the previous work and the obtained deuterium labeling experimental result. A new method for the synthesis of azaaromatic vinylcyclopropanes (VCPs) via palladium and Lewis acid catalyzed hydroamination of vinylidenecyclopropane-diesters (VDCP-diesters) under mild conditions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2cc03635e</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-0016-5211</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1359-7345
ispartof Chemical communications (Cambridge, England), 2022-09, Vol.58 (71), p.9926-9929
issn 1359-7345
1364-548X
language eng
recordid cdi_proquest_journals_2708676145
source Royal Society Of Chemistry Journals; Alma/SFX Local Collection
subjects Deuterium
Diesters
Indoles
Palladium
Phosphines
Pyrroles
Reaction mechanisms
Reagents
Substrates
title Palladium-catalyzed hydroamination of vinylidenecyclopropane-diester with pyrroles and indoles: an approach to azaaromatic vinylcyclopropanes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T13%3A32%3A14IST&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=Palladium-catalyzed%20hydroamination%20of%20vinylidenecyclopropane-diester%20with%20pyrroles%20and%20indoles:%20an%20approach%20to%20azaaromatic%20vinylcyclopropanes&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Yang,%20Ze-ren&rft.date=2022-09-01&rft.volume=58&rft.issue=71&rft.spage=9926&rft.epage=9929&rft.pages=9926-9929&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d2cc03635e&rft_dat=%3Cproquest_cross%3E2703983910%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=2708676145&rft_id=info:pmid/&rfr_iscdi=true