Copper‐Catalyzed N‐Arylation of Indoles and Anilines with Aryltrialkoxysilanes
Herein, we report an efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of various indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions. This silicon‐based protocol enables the efficient C−N cross‐coupling of indoles and anilines with user‐friendly orga...
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| Veröffentlicht in: | Asian journal of organic chemistry 2022-03, Vol.11 (3), p.n/a |
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| creator | Xie, Qi Zhang, Xiuqi Liu, Huijin Zhang, Fukuan Luo, Xuzhong Luo, Haiqing |
| description | Herein, we report an efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of various indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions. This silicon‐based protocol enables the efficient C−N cross‐coupling of indoles and anilines with user‐friendly organosilicon reagents by employing inexpensive and nontoxic Cu(OAc)2, which is efficient and practical without the addition of other ligands, bases, and metal oxidants. This transformation is compatible with a wide range of substrates, and typically proceeds with high efficiency as well as with good functional group compatibility. A plausible mechanism involving the formation of Cu(III) species in the reaction was tentatively proposed.
An efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions is reported. |
| doi_str_mv | 10.1002/ajoc.202100792 |
| format | Article |
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An efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions is reported.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202100792</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aniline ; anilines ; aryltrialkoxysilanes ; Base metal ; Copper ; copper-catalyzed ; Cross coupling ; Functional groups ; Indoles ; N-arylation ; N-arylindoles ; Organic chemistry ; Oxidizing agents ; Reagents ; Substrates</subject><ispartof>Asian journal of organic chemistry, 2022-03, Vol.11 (3), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-8543baa4b128da13efa63bc7cd022b858253eb70ca0962bd01937289e98116833</citedby><cites>FETCH-LOGICAL-c3172-8543baa4b128da13efa63bc7cd022b858253eb70ca0962bd01937289e98116833</cites><orcidid>0000-0003-2159-8403</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.202100792$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202100792$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Xie, Qi</creatorcontrib><creatorcontrib>Zhang, Xiuqi</creatorcontrib><creatorcontrib>Liu, Huijin</creatorcontrib><creatorcontrib>Zhang, Fukuan</creatorcontrib><creatorcontrib>Luo, Xuzhong</creatorcontrib><creatorcontrib>Luo, Haiqing</creatorcontrib><title>Copper‐Catalyzed N‐Arylation of Indoles and Anilines with Aryltrialkoxysilanes</title><title>Asian journal of organic chemistry</title><description>Herein, we report an efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of various indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions. This silicon‐based protocol enables the efficient C−N cross‐coupling of indoles and anilines with user‐friendly organosilicon reagents by employing inexpensive and nontoxic Cu(OAc)2, which is efficient and practical without the addition of other ligands, bases, and metal oxidants. This transformation is compatible with a wide range of substrates, and typically proceeds with high efficiency as well as with good functional group compatibility. A plausible mechanism involving the formation of Cu(III) species in the reaction was tentatively proposed.
An efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions is reported.</description><subject>Aniline</subject><subject>anilines</subject><subject>aryltrialkoxysilanes</subject><subject>Base metal</subject><subject>Copper</subject><subject>copper-catalyzed</subject><subject>Cross coupling</subject><subject>Functional groups</subject><subject>Indoles</subject><subject>N-arylation</subject><subject>N-arylindoles</subject><subject>Organic chemistry</subject><subject>Oxidizing agents</subject><subject>Reagents</subject><subject>Substrates</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkE1OwzAQhS0EElXplnUk1in2OIntZRTxU1RRCcHachJHuJg4OKlKWHEEzshJcFVUlsxm5mm-N5YfQucEzwnGcKnWrpoDhiCYgCM0ASJonHKSHh9mzE7RrO_XOBRjgoCYoIfCdZ32359fhRqUHT90Hd0HlfvRqsG4NnJNtGhrZ3UfqbaO8tZY0waxNcNztMMGb5R9ce9jb6wKmzN00ijb69lvn6Kn66vH4jZerm4WRb6MK0oYxDxNaKlUUhLgtSJUNyqjZcWqGgOUPOWQUl0yXCksMihrHD7BgAstOCEZp3SKLvZ3O-_eNrof5NptfBuelJAlOGGMAg_UfE9V3vW9143svHlVfpQEy110chedPEQXDGJv2Bqrx39omd-tij_vD9xrc9s</recordid><startdate>202203</startdate><enddate>202203</enddate><creator>Xie, Qi</creator><creator>Zhang, Xiuqi</creator><creator>Liu, Huijin</creator><creator>Zhang, Fukuan</creator><creator>Luo, Xuzhong</creator><creator>Luo, Haiqing</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2159-8403</orcidid></search><sort><creationdate>202203</creationdate><title>Copper‐Catalyzed N‐Arylation of Indoles and Anilines with Aryltrialkoxysilanes</title><author>Xie, Qi ; Zhang, Xiuqi ; Liu, Huijin ; Zhang, Fukuan ; Luo, Xuzhong ; Luo, Haiqing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-8543baa4b128da13efa63bc7cd022b858253eb70ca0962bd01937289e98116833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aniline</topic><topic>anilines</topic><topic>aryltrialkoxysilanes</topic><topic>Base metal</topic><topic>Copper</topic><topic>copper-catalyzed</topic><topic>Cross coupling</topic><topic>Functional groups</topic><topic>Indoles</topic><topic>N-arylation</topic><topic>N-arylindoles</topic><topic>Organic chemistry</topic><topic>Oxidizing agents</topic><topic>Reagents</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xie, Qi</creatorcontrib><creatorcontrib>Zhang, Xiuqi</creatorcontrib><creatorcontrib>Liu, Huijin</creatorcontrib><creatorcontrib>Zhang, Fukuan</creatorcontrib><creatorcontrib>Luo, Xuzhong</creatorcontrib><creatorcontrib>Luo, Haiqing</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xie, Qi</au><au>Zhang, Xiuqi</au><au>Liu, Huijin</au><au>Zhang, Fukuan</au><au>Luo, Xuzhong</au><au>Luo, Haiqing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper‐Catalyzed N‐Arylation of Indoles and Anilines with Aryltrialkoxysilanes</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2022-03</date><risdate>2022</risdate><volume>11</volume><issue>3</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>Herein, we report an efficient copper‐catalyzed aerobic Chan‐Lam type N‐arylation of various indoles and anilines with structurally diverse aryltrialkoxysilanes under mild conditions. This silicon‐based protocol enables the efficient C−N cross‐coupling of indoles and anilines with user‐friendly organosilicon reagents by employing inexpensive and nontoxic Cu(OAc)2, which is efficient and practical without the addition of other ligands, bases, and metal oxidants. This transformation is compatible with a wide range of substrates, and typically proceeds with high efficiency as well as with good functional group compatibility. A plausible mechanism involving the formation of Cu(III) species in the reaction was tentatively proposed.
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| subjects | Aniline anilines aryltrialkoxysilanes Base metal Copper copper-catalyzed Cross coupling Functional groups Indoles N-arylation N-arylindoles Organic chemistry Oxidizing agents Reagents Substrates |
| title | Copper‐Catalyzed N‐Arylation of Indoles and Anilines with Aryltrialkoxysilanes |
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