Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling

Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling

A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a proc...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2022-06, Vol.87 (11), p.7557-7564
Hauptverfasser: McClure, Timothy J., Saludares, Connor, Martinez, Gisela, Orozco, Cheyenne, Navarro, Raul
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7564
container_issue 11
container_start_page 7557
container_title Journal of organic chemistry
container_volume 87
creator McClure, Timothy J.
Saludares, Connor
Martinez, Gisela
Orozco, Cheyenne
Navarro, Raul
description A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields.
doi_str_mv 10.1021/acs.joc.2c00723
format Article
fullrecord <record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_proquest_miscellaneous_2665110985</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2665110985</sourcerecordid><originalsourceid>FETCH-LOGICAL-a695-48663e57252f5beb055721f660358597ddba6c5a22463d7aa48a932106331b9f3</originalsourceid><addsrcrecordid>eNotkM1OwzAQhC0EEqVw5uojEkqw17GTcCvlV6oAid4jx3Goi4lDnCDaE-_AG_IkmLZ7mJFGn1ajQeiUkpgSoBdS-XjpVAyKkBTYHhpRDiQSOUn20YgQgIiBYIfoyPslCcc5HyFzrZXsSve1srI3nxpPrF1Zo4K_bSLXYFfj50W_kNZU2l_il16Wxpq1rvCVbtYb-nFQVrt2Yaz2uHYd9i37_f4JiqduaK1pXo_RQS2t1yc7H6P57c18eh_Nnu4eppNZJEXOoyQTgmmeAoeal7oMLVOgtRCE8YznaVWVUiguARLBqlTKJJM5A0oEY7TMazZGZ9u3bec-Bu374t14pa2VjXaDL0AITinJMx7Q8y0apiuWbuia0KugpPjfs9iGqtjtyf4ASjtq7w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2665110985</pqid></control><display><type>article</type><title>Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling</title><source>American Chemical Society Journals</source><creator>McClure, Timothy J. ; Saludares, Connor ; Martinez, Gisela ; Orozco, Cheyenne ; Navarro, Raul</creator><creatorcontrib>McClure, Timothy J. ; Saludares, Connor ; Martinez, Gisela ; Orozco, Cheyenne ; Navarro, Raul</creatorcontrib><description>A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c00723</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2022-06, Vol.87 (11), p.7557-7564</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-7912-2929</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.2c00723$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c00723$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids></links><search><creatorcontrib>McClure, Timothy J.</creatorcontrib><creatorcontrib>Saludares, Connor</creatorcontrib><creatorcontrib>Martinez, Gisela</creatorcontrib><creatorcontrib>Orozco, Cheyenne</creatorcontrib><creatorcontrib>Navarro, Raul</creatorcontrib><title>Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNotkM1OwzAQhC0EEqVw5uojEkqw17GTcCvlV6oAid4jx3Goi4lDnCDaE-_AG_IkmLZ7mJFGn1ajQeiUkpgSoBdS-XjpVAyKkBTYHhpRDiQSOUn20YgQgIiBYIfoyPslCcc5HyFzrZXsSve1srI3nxpPrF1Zo4K_bSLXYFfj50W_kNZU2l_il16Wxpq1rvCVbtYb-nFQVrt2Yaz2uHYd9i37_f4JiqduaK1pXo_RQS2t1yc7H6P57c18eh_Nnu4eppNZJEXOoyQTgmmeAoeal7oMLVOgtRCE8YznaVWVUiguARLBqlTKJJM5A0oEY7TMazZGZ9u3bec-Bu374t14pa2VjXaDL0AITinJMx7Q8y0apiuWbuia0KugpPjfs9iGqtjtyf4ASjtq7w</recordid><startdate>20220603</startdate><enddate>20220603</enddate><creator>McClure, Timothy J.</creator><creator>Saludares, Connor</creator><creator>Martinez, Gisela</creator><creator>Orozco, Cheyenne</creator><creator>Navarro, Raul</creator><general>American Chemical Society</general><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7912-2929</orcidid></search><sort><creationdate>20220603</creationdate><title>Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling</title><author>McClure, Timothy J. ; Saludares, Connor ; Martinez, Gisela ; Orozco, Cheyenne ; Navarro, Raul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a695-48663e57252f5beb055721f660358597ddba6c5a22463d7aa48a932106331b9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McClure, Timothy J.</creatorcontrib><creatorcontrib>Saludares, Connor</creatorcontrib><creatorcontrib>Martinez, Gisela</creatorcontrib><creatorcontrib>Orozco, Cheyenne</creatorcontrib><creatorcontrib>Navarro, Raul</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McClure, Timothy J.</au><au>Saludares, Connor</au><au>Martinez, Gisela</au><au>Orozco, Cheyenne</au><au>Navarro, Raul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2022-06-03</date><risdate>2022</risdate><volume>87</volume><issue>11</issue><spage>7557</spage><epage>7564</epage><pages>7557-7564</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A new family of stabilized benzylic nucleophiles for the palladium-catalyzed decarboxylative allylic alkylation reaction has been developed. Allyl esters derived from 3-carboxyphthalides were found to undergo palladium-catalyzed deallylation and decarboxylation under mild reaction conditions, a process facilitated by the formation of a stabilized aromatic anion. The regioselective allylic coupling of this intermediate afforded a variety of functionalized phthalides in 73–96% yields.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.joc.2c00723</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-7912-2929</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2022-06, Vol.87 (11), p.7557-7564
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2665110985
source American Chemical Society Journals
title Decarboxylative Allylic Alkylation of Phthalides: Stabilized Benzylic Nucleophiles for sp3–sp3 Coupling
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T01%3A20%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Decarboxylative%20Allylic%20Alkylation%20of%20Phthalides:%20Stabilized%20Benzylic%20Nucleophiles%20for%20sp3%E2%80%93sp3%20Coupling&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=McClure,%20Timothy%20J.&rft.date=2022-06-03&rft.volume=87&rft.issue=11&rft.spage=7557&rft.epage=7564&rft.pages=7557-7564&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.2c00723&rft_dat=%3Cproquest_acs_j%3E2665110985%3C/proquest_acs_j%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2665110985&rft_id=info:pmid/&rfr_iscdi=true