Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxid...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2018-01, Vol.360 (2), p.272-277 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 277 |
|---|---|
| container_issue | 2 |
| container_start_page | 272 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 360 |
| creator | Zhang, Xinglu Liu, Zhiqiang Gao, Yu Li, Feng Tian, Yaming Li, Chunju Jia, Xueshun Li, Jian |
| description | A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C−C and C−O bond‐forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. |
| doi_str_mv | 10.1002/adsc.201700953 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1988016631</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1988016631</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3543-b982adedbc7a81e0f6eec6153201a713a96c02ef757a8b336cf2ab8f58b493833</originalsourceid><addsrcrecordid>eNqFkM9PwjAcxRujiYhePTfxPGxXtrVHMn-RkGBEzk3XfYfFueK6Afvv7UTx6Knf9n3ea74PoWtKRpSQ8FblTo9CQhNCRMRO0IDGNArGNBanxzki5-jCuTXxGE-SAWoXUIJuzBbwfG9y9T2ltt2UplrhF1BesxW2BZ46qztVmRwcXrpefYbaeg9g5fBiZxr9prIS8KR870of5AlV5f3V7n8ffOAKquYSnRWqdHD1cw7R8uH-NX0KZvPHaTqZBZpFYxZkgocqhzzTieIUSBEDaL8I81uqhDIlYk1CKJLI6xljsS5ClfEi4tlYMM7YEN0ccje1_WzBNXJt27ryX0oqOCc0jhn11OhA6do6V0MhN7X5UHUnKZF9tbKvVh6r9QZxMOxMCd0_tJzcLdI_7xeuAX81</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1988016631</pqid></control><display><type>article</type><title>Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent</title><source>Wiley Online Library All Journals</source><creator>Zhang, Xinglu ; Liu, Zhiqiang ; Gao, Yu ; Li, Feng ; Tian, Yaming ; Li, Chunju ; Jia, Xueshun ; Li, Jian</creator><creatorcontrib>Zhang, Xinglu ; Liu, Zhiqiang ; Gao, Yu ; Li, Feng ; Tian, Yaming ; Li, Chunju ; Jia, Xueshun ; Li, Jian</creatorcontrib><description>A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C−C and C−O bond‐forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201700953</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Aliphatic compounds ; Alkylation ; Catalysis ; Catalysts ; Chemical industry ; Coupling ; Iron ; Isocyanide ; Oxidation ; Peroxide ; Radical</subject><ispartof>Advanced synthesis & catalysis, 2018-01, Vol.360 (2), p.272-277</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3543-b982adedbc7a81e0f6eec6153201a713a96c02ef757a8b336cf2ab8f58b493833</citedby><cites>FETCH-LOGICAL-c3543-b982adedbc7a81e0f6eec6153201a713a96c02ef757a8b336cf2ab8f58b493833</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%2Fadsc.201700953$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201700953$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids></links><search><creatorcontrib>Zhang, Xinglu</creatorcontrib><creatorcontrib>Liu, Zhiqiang</creatorcontrib><creatorcontrib>Gao, Yu</creatorcontrib><creatorcontrib>Li, Feng</creatorcontrib><creatorcontrib>Tian, Yaming</creatorcontrib><creatorcontrib>Li, Chunju</creatorcontrib><creatorcontrib>Jia, Xueshun</creatorcontrib><creatorcontrib>Li, Jian</creatorcontrib><title>Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent</title><title>Advanced synthesis & catalysis</title><description>A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C−C and C−O bond‐forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used.</description><subject>Aliphatic compounds</subject><subject>Alkylation</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical industry</subject><subject>Coupling</subject><subject>Iron</subject><subject>Isocyanide</subject><subject>Oxidation</subject><subject>Peroxide</subject><subject>Radical</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkM9PwjAcxRujiYhePTfxPGxXtrVHMn-RkGBEzk3XfYfFueK6Afvv7UTx6Knf9n3ea74PoWtKRpSQ8FblTo9CQhNCRMRO0IDGNArGNBanxzki5-jCuTXxGE-SAWoXUIJuzBbwfG9y9T2ltt2UplrhF1BesxW2BZ46qztVmRwcXrpefYbaeg9g5fBiZxr9prIS8KR870of5AlV5f3V7n8ffOAKquYSnRWqdHD1cw7R8uH-NX0KZvPHaTqZBZpFYxZkgocqhzzTieIUSBEDaL8I81uqhDIlYk1CKJLI6xljsS5ClfEi4tlYMM7YEN0ccje1_WzBNXJt27ryX0oqOCc0jhn11OhA6do6V0MhN7X5UHUnKZF9tbKvVh6r9QZxMOxMCd0_tJzcLdI_7xeuAX81</recordid><startdate>20180117</startdate><enddate>20180117</enddate><creator>Zhang, Xinglu</creator><creator>Liu, Zhiqiang</creator><creator>Gao, Yu</creator><creator>Li, Feng</creator><creator>Tian, Yaming</creator><creator>Li, Chunju</creator><creator>Jia, Xueshun</creator><creator>Li, Jian</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20180117</creationdate><title>Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent</title><author>Zhang, Xinglu ; Liu, Zhiqiang ; Gao, Yu ; Li, Feng ; Tian, Yaming ; Li, Chunju ; Jia, Xueshun ; Li, Jian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3543-b982adedbc7a81e0f6eec6153201a713a96c02ef757a8b336cf2ab8f58b493833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aliphatic compounds</topic><topic>Alkylation</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical industry</topic><topic>Coupling</topic><topic>Iron</topic><topic>Isocyanide</topic><topic>Oxidation</topic><topic>Peroxide</topic><topic>Radical</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xinglu</creatorcontrib><creatorcontrib>Liu, Zhiqiang</creatorcontrib><creatorcontrib>Gao, Yu</creatorcontrib><creatorcontrib>Li, Feng</creatorcontrib><creatorcontrib>Tian, Yaming</creatorcontrib><creatorcontrib>Li, Chunju</creatorcontrib><creatorcontrib>Jia, Xueshun</creatorcontrib><creatorcontrib>Li, Jian</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xinglu</au><au>Liu, Zhiqiang</au><au>Gao, Yu</au><au>Li, Feng</au><au>Tian, Yaming</au><au>Li, Chunju</au><au>Jia, Xueshun</au><au>Li, Jian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-01-17</date><risdate>2018</risdate><volume>360</volume><issue>2</issue><spage>272</spage><epage>277</epage><pages>272-277</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C−C and C−O bond‐forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201700953</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2018-01, Vol.360 (2), p.272-277 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_1988016631 |
| source | Wiley Online Library All Journals |
| subjects | Aliphatic compounds Alkylation Catalysis Catalysts Chemical industry Coupling Iron Isocyanide Oxidation Peroxide Radical |
| title | Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T15%3A44%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=Selective%20Oxidative%20Coupling%20Reaction%20of%20Isocyanides%20Using%20Peroxide%20as%20Switchable%20Alkylating%20and%20Alkoxylating%20Reagent&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Zhang,%20Xinglu&rft.date=2018-01-17&rft.volume=360&rft.issue=2&rft.spage=272&rft.epage=277&rft.pages=272-277&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201700953&rft_dat=%3Cproquest_cross%3E1988016631%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=1988016631&rft_id=info:pmid/&rfr_iscdi=true |