One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis

Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the pre...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2017-01, Vol.56 (5), p.1361-1364
Hauptverfasser: Ozaki, Kyohei, Murai, Keiichiro, Matsuoka, Wataru, Kawasumi, Katsuaki, Ito, Hideto, Itami, Kenichiro
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1364
container_issue 5
container_start_page 1361
container_title Angewandte Chemie International Edition
container_volume 56
creator Ozaki, Kyohei
Murai, Keiichiro
Matsuoka, Wataru
Kawasumi, Katsuaki
Ito, Hideto
Itami, Kenichiro
description Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group tolerance. Furthermore, double π‐extension reactions of 1,4‐bis(phenylethynyl)benzene and diphenyl‐1,3‐butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes. Extending circumstances: An efficient one‐step annulative π‐extension reaction of alkynes provides facile access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system, a variety of diarylacetylenes are transformed through the use of dibenzosiloles or dibenzogermoles as π‐extending agents into 9,10‐diarylphenanthrenes with good functional‐group tolerance.
doi_str_mv 10.1002/anie.201610374
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1851301170</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1851301170</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3454-52a38ef216ec61f958bd02a056dc8a722630cfb771a6b746bd59918c474737dd3</originalsourceid><addsrcrecordid>eNqFkE1OwzAQRi0EglLYskRZsknrnyR2l1UpUKkCJGAdOckEDI5d4gQIbDgCN-MOnARDCyxZzejTm0-jh9AewQOCMR1Ko2BAMUkIZjxaQz0SUxIyztm63yPGQi5isoW2nbv1vBA42URbVGCMmYh76OXMwMfr20UDi2BsTKtlox4geH_14fSpAeOUNYEtg7G-6wy44FE1N8GhysA8W6e01T6z9U9yDXX1HWVdcC61loVqq6H1ZfmNtrX_VgcT2UjdOeV20EYptYPd1eyjq6Pp5eQknJ8dzybjeZizKI7CmEomoKQkgTwh5SgWWYGpxHFS5EJyShOG8zLjnMgk41GSFfFoREQe8YgzXhSsjw6WvYva3rfgmrRSLgf_nQHbupR4QwwTwrFHB0s0r61zNZTpolaVrLuU4PRLePolPP0V7g_2V91tVkHxi_8Y9sBoCTwqDd0_den4dDb9K_8Ell-R5A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1851301170</pqid></control><display><type>article</type><title>One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis</title><source>Wiley Journals</source><creator>Ozaki, Kyohei ; Murai, Keiichiro ; Matsuoka, Wataru ; Kawasumi, Katsuaki ; Ito, Hideto ; Itami, Kenichiro</creator><creatorcontrib>Ozaki, Kyohei ; Murai, Keiichiro ; Matsuoka, Wataru ; Kawasumi, Katsuaki ; Ito, Hideto ; Itami, Kenichiro</creatorcontrib><description>Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group tolerance. Furthermore, double π‐extension reactions of 1,4‐bis(phenylethynyl)benzene and diphenyl‐1,3‐butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes. Extending circumstances: An efficient one‐step annulative π‐extension reaction of alkynes provides facile access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system, a variety of diarylacetylenes are transformed through the use of dibenzosiloles or dibenzogermoles as π‐extending agents into 9,10‐diarylphenanthrenes with good functional‐group tolerance.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201610374</identifier><identifier>PMID: 28000385</identifier><language>eng</language><publisher>Germany</publisher><subject>alkynes ; dibenzosiloles ; palladium ; polycyclic aromatic hydrocarbons ; π-extension</subject><ispartof>Angewandte Chemie International Edition, 2017-01, Vol.56 (5), p.1361-1364</ispartof><rights>2017 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3454-52a38ef216ec61f958bd02a056dc8a722630cfb771a6b746bd59918c474737dd3</citedby><cites>FETCH-LOGICAL-c3454-52a38ef216ec61f958bd02a056dc8a722630cfb771a6b746bd59918c474737dd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201610374$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201610374$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28000385$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ozaki, Kyohei</creatorcontrib><creatorcontrib>Murai, Keiichiro</creatorcontrib><creatorcontrib>Matsuoka, Wataru</creatorcontrib><creatorcontrib>Kawasumi, Katsuaki</creatorcontrib><creatorcontrib>Ito, Hideto</creatorcontrib><creatorcontrib>Itami, Kenichiro</creatorcontrib><title>One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group tolerance. Furthermore, double π‐extension reactions of 1,4‐bis(phenylethynyl)benzene and diphenyl‐1,3‐butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes. Extending circumstances: An efficient one‐step annulative π‐extension reaction of alkynes provides facile access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system, a variety of diarylacetylenes are transformed through the use of dibenzosiloles or dibenzogermoles as π‐extending agents into 9,10‐diarylphenanthrenes with good functional‐group tolerance.</description><subject>alkynes</subject><subject>dibenzosiloles</subject><subject>palladium</subject><subject>polycyclic aromatic hydrocarbons</subject><subject>π-extension</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkE1OwzAQRi0EglLYskRZsknrnyR2l1UpUKkCJGAdOckEDI5d4gQIbDgCN-MOnARDCyxZzejTm0-jh9AewQOCMR1Ko2BAMUkIZjxaQz0SUxIyztm63yPGQi5isoW2nbv1vBA42URbVGCMmYh76OXMwMfr20UDi2BsTKtlox4geH_14fSpAeOUNYEtg7G-6wy44FE1N8GhysA8W6e01T6z9U9yDXX1HWVdcC61loVqq6H1ZfmNtrX_VgcT2UjdOeV20EYptYPd1eyjq6Pp5eQknJ8dzybjeZizKI7CmEomoKQkgTwh5SgWWYGpxHFS5EJyShOG8zLjnMgk41GSFfFoREQe8YgzXhSsjw6WvYva3rfgmrRSLgf_nQHbupR4QwwTwrFHB0s0r61zNZTpolaVrLuU4PRLePolPP0V7g_2V91tVkHxi_8Y9sBoCTwqDd0_den4dDb9K_8Ell-R5A</recordid><startdate>20170124</startdate><enddate>20170124</enddate><creator>Ozaki, Kyohei</creator><creator>Murai, Keiichiro</creator><creator>Matsuoka, Wataru</creator><creator>Kawasumi, Katsuaki</creator><creator>Ito, Hideto</creator><creator>Itami, Kenichiro</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20170124</creationdate><title>One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis</title><author>Ozaki, Kyohei ; Murai, Keiichiro ; Matsuoka, Wataru ; Kawasumi, Katsuaki ; Ito, Hideto ; Itami, Kenichiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3454-52a38ef216ec61f958bd02a056dc8a722630cfb771a6b746bd59918c474737dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>alkynes</topic><topic>dibenzosiloles</topic><topic>palladium</topic><topic>polycyclic aromatic hydrocarbons</topic><topic>π-extension</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ozaki, Kyohei</creatorcontrib><creatorcontrib>Murai, Keiichiro</creatorcontrib><creatorcontrib>Matsuoka, Wataru</creatorcontrib><creatorcontrib>Kawasumi, Katsuaki</creatorcontrib><creatorcontrib>Ito, Hideto</creatorcontrib><creatorcontrib>Itami, Kenichiro</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ozaki, Kyohei</au><au>Murai, Keiichiro</au><au>Matsuoka, Wataru</au><au>Kawasumi, Katsuaki</au><au>Ito, Hideto</au><au>Itami, Kenichiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-01-24</date><risdate>2017</risdate><volume>56</volume><issue>5</issue><spage>1361</spage><epage>1364</epage><pages>1361-1364</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one‐step annulative π‐extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system and dibenzosiloles or dibenzogermoles as π‐extending agents, a variety of diarylacetylenes are transformed successfully into 9,10‐diarylphenanthrenes in a single step with good functional‐group tolerance. Furthermore, double π‐extension reactions of 1,4‐bis(phenylethynyl)benzene and diphenyl‐1,3‐butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes. Extending circumstances: An efficient one‐step annulative π‐extension reaction of alkynes provides facile access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o‐chloranil catalyst system, a variety of diarylacetylenes are transformed through the use of dibenzosiloles or dibenzogermoles as π‐extending agents into 9,10‐diarylphenanthrenes with good functional‐group tolerance.</abstract><cop>Germany</cop><pmid>28000385</pmid><doi>10.1002/anie.201610374</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2017-01, Vol.56 (5), p.1361-1364
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_1851301170
source Wiley Journals
subjects alkynes
dibenzosiloles
palladium
polycyclic aromatic hydrocarbons
π-extension
title One‐Step Annulative π‐Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o‐chloranil Catalysis
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T06%3A06%3A44IST&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=One%E2%80%90Step%20Annulative%20%CF%80%E2%80%90Extension%20of%20Alkynes%20with%20Dibenzosiloles%20or%20Dibenzogermoles%20by%20Palladium/o%E2%80%90chloranil%20Catalysis&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Ozaki,%20Kyohei&rft.date=2017-01-24&rft.volume=56&rft.issue=5&rft.spage=1361&rft.epage=1364&rft.pages=1361-1364&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201610374&rft_dat=%3Cproquest_cross%3E1851301170%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=1851301170&rft_id=info:pmid/28000385&rfr_iscdi=true