Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles
A lanthanide‐catalyzed intermolecular hydroamination of 2‐alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild re...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2018-12, Vol.13 (23), p.3681-3690 |
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| creator | Ye, Pengqing Shao, Yinlin Xie, Leping Shen, Keting Cheng, Tianxing Chen, Jiuxi |
| description | A lanthanide‐catalyzed intermolecular hydroamination of 2‐alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance. This methodology has also been successfully applied to the construction of other nitrogen‐containing compounds, such as 5 H‐imidazo[2,1‐a]isoindoles and isoquinolines. A plausible mechanism for the formation of aminoisoindoles involving initial N−H activation by a lanthanide complex followed by C≡N insertion into a Ln−N bond to form an amidinate lanthanide intermediate, which undergoes the cyclization is proposed.
N−H Activation: A lanthanide‐catalyzed tandem hydroamination/cyclization reaction was developed for the construction of aminoisoindoles as well as other nitrogen‐containing compounds, such as 5H‐imidazo[2,1‐a]isoindoles and isoquinolines, in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance. |
| doi_str_mv | 10.1002/asia.201801252 |
| format | Article |
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N−H Activation: A lanthanide‐catalyzed tandem hydroamination/cyclization reaction was developed for the construction of aminoisoindoles as well as other nitrogen‐containing compounds, such as 5H‐imidazo[2,1‐a]isoindoles and isoquinolines, in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201801252</identifier><identifier>PMID: 30209887</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>2-alkynylbenzonitriles ; Amines ; aminoisoindoles ; Chemical synthesis ; Chemistry ; Functional groups ; Insertion ; lanthanide-catalyzed ; Nitrogen ; secondary amines ; tandem reaction</subject><ispartof>Chemistry, an Asian journal, 2018-12, Vol.13 (23), p.3681-3690</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-c4102-6df5d767d1b1ebae88bdbec2fd228ce15f25494032cac4d464767680b27a19273</citedby><cites>FETCH-LOGICAL-c4102-6df5d767d1b1ebae88bdbec2fd228ce15f25494032cac4d464767680b27a19273</cites><orcidid>0000-0001-6666-9813 ; 0000-0003-1935-0345</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%2Fasia.201801252$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201801252$$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/30209887$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ye, Pengqing</creatorcontrib><creatorcontrib>Shao, Yinlin</creatorcontrib><creatorcontrib>Xie, Leping</creatorcontrib><creatorcontrib>Shen, Keting</creatorcontrib><creatorcontrib>Cheng, Tianxing</creatorcontrib><creatorcontrib>Chen, Jiuxi</creatorcontrib><title>Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles</title><title>Chemistry, an Asian journal</title><addtitle>Chem Asian J</addtitle><description>A lanthanide‐catalyzed intermolecular hydroamination of 2‐alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance. This methodology has also been successfully applied to the construction of other nitrogen‐containing compounds, such as 5 H‐imidazo[2,1‐a]isoindoles and isoquinolines. A plausible mechanism for the formation of aminoisoindoles involving initial N−H activation by a lanthanide complex followed by C≡N insertion into a Ln−N bond to form an amidinate lanthanide intermediate, which undergoes the cyclization is proposed.
N−H Activation: A lanthanide‐catalyzed tandem hydroamination/cyclization reaction was developed for the construction of aminoisoindoles as well as other nitrogen‐containing compounds, such as 5H‐imidazo[2,1‐a]isoindoles and isoquinolines, in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance.</description><subject>2-alkynylbenzonitriles</subject><subject>Amines</subject><subject>aminoisoindoles</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Functional groups</subject><subject>Insertion</subject><subject>lanthanide-catalyzed</subject><subject>Nitrogen</subject><subject>secondary amines</subject><subject>tandem reaction</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkU1LwzAYx4Mobk6vHqXgxUtnkr6l3srwZTDwsAneSto8ZZltMpuW0Z38CH5GP4kpmxO8eMoD-f1_Cc8foUuCxwRjesuN5GOKCcOEBvQIDQkLietH5PX4MFM2QGfGrDAOKI7ZKRp4uB9YNESbGVfNkisp4Ovjc8IbXnZbEM6CKwGVM1UG6kZq5ejCmUOuleB15ySVVGCcjWyWDrW5pHzrVFdmoLZayaaWJZg7Z95ZNRhp-nAf0dJoqYS2t-fopOClgYv9OUIvD_eLyZM7e36cTpKZm_sEUzcURSCiMBIkI5BxYCwTGeS0EJSyHEhQ0MCPfezRnOe-8EPfwiHDGY04iWnkjdDNzruu9XsLpkkraXIoS65AtyalBHthGNu3LHr9B13ptlb2d5by44CxIMKWGu-ovNbG1FCk61pWdikpwWlfSdpXkh4qsYGrvbbNKhAH_KcDC8Q7YGPX1v2jS5P5NPmVfwOZkpuX</recordid><startdate>20181204</startdate><enddate>20181204</enddate><creator>Ye, Pengqing</creator><creator>Shao, Yinlin</creator><creator>Xie, Leping</creator><creator>Shen, Keting</creator><creator>Cheng, Tianxing</creator><creator>Chen, Jiuxi</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6666-9813</orcidid><orcidid>https://orcid.org/0000-0003-1935-0345</orcidid></search><sort><creationdate>20181204</creationdate><title>Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles</title><author>Ye, Pengqing ; Shao, Yinlin ; Xie, Leping ; Shen, Keting ; Cheng, Tianxing ; Chen, Jiuxi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-6df5d767d1b1ebae88bdbec2fd228ce15f25494032cac4d464767680b27a19273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>2-alkynylbenzonitriles</topic><topic>Amines</topic><topic>aminoisoindoles</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Functional groups</topic><topic>Insertion</topic><topic>lanthanide-catalyzed</topic><topic>Nitrogen</topic><topic>secondary amines</topic><topic>tandem reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ye, Pengqing</creatorcontrib><creatorcontrib>Shao, Yinlin</creatorcontrib><creatorcontrib>Xie, Leping</creatorcontrib><creatorcontrib>Shen, Keting</creatorcontrib><creatorcontrib>Cheng, Tianxing</creatorcontrib><creatorcontrib>Chen, Jiuxi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ye, Pengqing</au><au>Shao, Yinlin</au><au>Xie, Leping</au><au>Shen, Keting</au><au>Cheng, Tianxing</au><au>Chen, Jiuxi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem Asian J</addtitle><date>2018-12-04</date><risdate>2018</risdate><volume>13</volume><issue>23</issue><spage>3681</spage><epage>3690</epage><pages>3681-3690</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>A lanthanide‐catalyzed intermolecular hydroamination of 2‐alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance. This methodology has also been successfully applied to the construction of other nitrogen‐containing compounds, such as 5 H‐imidazo[2,1‐a]isoindoles and isoquinolines. A plausible mechanism for the formation of aminoisoindoles involving initial N−H activation by a lanthanide complex followed by C≡N insertion into a Ln−N bond to form an amidinate lanthanide intermediate, which undergoes the cyclization is proposed.
N−H Activation: A lanthanide‐catalyzed tandem hydroamination/cyclization reaction was developed for the construction of aminoisoindoles as well as other nitrogen‐containing compounds, such as 5H‐imidazo[2,1‐a]isoindoles and isoquinolines, in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30209887</pmid><doi>10.1002/asia.201801252</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-6666-9813</orcidid><orcidid>https://orcid.org/0000-0003-1935-0345</orcidid></addata></record> |
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| subjects | 2-alkynylbenzonitriles Amines aminoisoindoles Chemical synthesis Chemistry Functional groups Insertion lanthanide-catalyzed Nitrogen secondary amines tandem reaction |
| title | Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles |
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